We’re living through a strange paradox in GTM hiring: It has never been easier to apply for a job, yet it has never been harder to get noticed. AI has commoditized the application process, making obsolete the way you found a job just a few years ago.

I wanted to understand this shift so I interviewed GTM leaders who recently signed offer letters. I asked them what AI tools and tactics they found most effective. I asked what they noticed is different about job searching today. Then I condensed down those answers for you below.

Some of their insights I found surprising; others are timeless fundamentals that matter more now than ever.

I hope you can put these insights to use find your next role.

Glen

What is the biggest shift you noticed in the hiring process compared to your last job search?

• The power of your network - “AI makes it even easier to apply to online job postings. The way in was through my connections. I would not have landed this job without a connection on the inside.”

• A bias for generalists & builders - “Many roles I explored in the past were quite niche but increasingly there’s demand for folks who can generalize across different types of partnerships and be fluid and flexible in how they work. There is more demand than ever for generalists and builders.”

• Outreach directly to hiring managers - “One shift I noticed was the effectiveness of reaching out directly to the hiring manager to jump start an interview process. This could be because my network and relationships with hiring managers is broader than it was before when I found the process more recruiter driven, or it could be because companies have reduced their number of recruiters.”

• Showcase your use of AI - “The same way so many companies are trying to showcase how they are AI-first, the same applies to job candidates. Personally, I did not find that hiring managers explicitly asked me about AI. So I found ways to work it into the conversation organically, to showcase something I built with AI at work or outside of work.”

• The drawbacks of tenure - “Tenure is no longer an advantage when companies prioritize AI-driven efficiency above all. My experience deemed me as too expensive to get past some recruiter screens.”

What was the single most helpful AI tool or prompt you used during your job search? How did it help you?

• AI job searching - “Checkout AI Apply and Jack & Jill. They harness AI for you to help you find jobs, enhance your resume, etc, like an AI-native version of Indeed or Linkedin jobs.”

• Use LinkedIn search like an LLM - “The search bar on LinkedIn Jobs is now an AI prompt tool. Except the UI is rubbish so you don't know that. Treat it like you would ChatGPT, Claude or Gemini. Write as detailed a description of what kind of job you’re looking for and the results will be better.”

• Interview prep - “I used AI for pre-interview research and post-interview follow-up. Before interviews I leveraged AI for deep research on a company and on the interviewer based on their role.I used AI to anticipate questions and prepare answers as well as organize my own questions.Then I would have it generate an interview prep-kit with everything I needed in one file for that interview.”

• Resume-writing - “ChatGPT & Claude helped me tighten all of my writing around professional experience, which was a huge help.”

• Interview storytelling - “I’d ask AI to review my resume and pose potential questions I might face and offer answers for me to consider using.”

What is a job searching tactic that may have worked in 2022 but feels obsolete today?

• Cold applying on sites like Indeed and LinkedIn.

• OTW - “I’m not sure if it ever worked, but the ‘Open To Work’ badge on LinkedIn I’ve never really been super comfortable with or bullish on.”

• The elegant resumes - “The beautifully formatted resume is now a liability. Resumes must be optimized for ATS.”

• Cover letters - “With AI, I think they have lost whatever limited weight they once carried.”

• Hotmail - “This was true in 2022 but it’s even more true today: you aren’t likely to land a job at that hot company with your Hotmail or Yahoo email address. Use Gmail or a personalized email address (e.g. jane@janedoe.ai).”

In a market changing this rapidly, how did you validate that the company you chose to join is actually well-positioned for this AI era?

• Diligence is tough - “Unless it’s an AI-native company, or a massive global org like Google, knowing what is real and what is vaporware is not easy. You can ask questions in the interview process, you can do your research, but its still not a guarantee.”

• Kick the tires - “I did a significant amount of research into the company’s differentiation in the market coupled with the metrics: the company had A/B or lift-tested its predictive AI over 600 times, with real customers, against their BAU, and won nearly every time.”

• The people - “I prioritize who I’ll be working with and for, so I put a lot of weight on the discussions I had with those leaders. I also sought out the opinions of people who are more deeply embedded (and invested) in AI to get their point of view on the companies I’m considering joining.”

• The business model - “I didn’t do this expliclty. What I liked about my role is that it is selling shovels and jeans to the miners. Not a miner itself. Less dependent on the model or IDE of the day.”

• Go with what you know - “I may have been at a slight advantage here as I have known the company and the co-founders for many years. I know the path they’ve been on to help define and drive how AI will be used in every size of business in the future.”

So much of job searching is still about making human connections (and NOT using AI). What is one thing you did in your job search unrelated to AI that you think made a difference?

• Let your network know that you’re looking - “Simply letting my network know that I was looking to make my next move - this included former co-workers and current co-workers and partners (that I trusted to be discreet). When I saw a partnership leader that I respected move to a new company, I would reach out to congratulate them and also plant a seed that I’d be interested in having a chat if they’re planning to hire or build out a team.”

• Thank you notes - “I still love a good ol’ thank you note after an interview. I tried to remember at least one personal piece of info from everyone I spoke with, and wove that into my thank you note.”

• Connections at the top - “Human connections are still everything - if I didn’t know the co-founders and also hadn’t been a big advocate of the company since the early days, I’m not sure I would have landed this role.”

• Never Search Alone - “I am a huge advocate of a program & book called Never Search Alone, by Phyl Terry. Phyl’s book is common sense guidance for anyone navigating a career pivot or job search, and he’s also built an enormous network of Job Search Councils, which meet regularly in small groups so people can help others who are going through similar journeys. I cannot advocate enough for the Never Search Alone program. You can get the book from the library and participate for free. I got more value from NSA than from any high-priced career coach or resume service.”

Anything else you want to offer other job searchers?

• Start Now - “The best time to connect with that co-worker, a person you met at the conference, former classmate, etc. was yesterday. The second best time is now.”

• Your network matters now more than ever - “You’ve got to activate your network of relationships. But make it easy for people to help you. Be specific about what you’re looking for and how you’d like that person to help.”

• Do the work - “Using AI will only get you so far. It is really good for helping to structure your thoughts and for preparing for interviews, but it shouldn’t replace your thoughts. You will be interviewed by other humans, and they will be able to identify if you’re giving them AI-generated or insincere answers pretty quickly.”

• Find meaning outside of your job search - “Job searching is an emotional roller-coaster. Find something outside of your job search to invest your time and energy to bring you joy and fulfillment, or at least serve as a distraction. Coach a youth team. Build a cabinet. Learn guitar.”

I found a stark example in a surprising place: Instagram.

Olivia Ferney is a 25-year old travel agent for the uber-wealthy with a massive social media following (@travelswithlivi).

Olivia’s 1M followers tune in to see the absurd demands of the 1% (think: $250K wire transfer for NYC Fashion Week and specialty limes shipped to a luxury hotel on a remote island). Her videos are an entertaining and nauseating window into a world where the mega-rich live like royalty.

But her most interesting video (to me) isn't about luxury travel. It is a video of a negotiation with a rich client who pressured her to cross a personal line.

An Indecent Request

In the video below, one of Olivia’s clients named Levi calls her asking for help getting a date with a hostess at a restaurant he just left … while he was on a date with another woman.

What stands out about this negotiation isn’t just the absurdity of a man asking his travel agent to secure him a date. This is a conversation between a young woman who sets a firm boundary with a wealthy man who she works for.

The cards appear to be stacked against Olivia here.

But she handles the situation firmly with calm and charm.

The Negotiation

You can watch this negotiation here (2 mins) or read this transcript:

Levi: I wanted to ask you … it’s a little bit of an awkward request but the hostess was gorgeous. And obviously, I was on a date, so I couldn’t do much. But I would like for you to inquire for me and find out … some information. Is she single? And, more importantly, if you could setup a date for her and I.

Olivia (pushback #1): That is 1000% out of my comfort zone. I don’t handle any stuff like that whatsoever. Why don’t you … we can make a reservation there tonight and you can ask her yourself.

Levi: Yeah, I would really like your help with this one. I know you don’t feel too comfortable with this one. I think your support would be greatly appreciated and would go a long way.

Olivia (pushback #2): Of course, and thank you for having that trust in me. Again, that is so far out of the realm of services I provide. Honestly, being a woman, I think you should put on a good outfit. Put on that Levi charm.

Levi: Alright, not to push any buttons, I did see that brat’s video that was on your instagram [reference to a separate video Olivia posted, a conversation with one of her client’s children] and unlike her, you work for me, Liv … and not for my father. So I am going to respectfully ask that you reconsider and call the hotel and get her information for me.

Olivia (pushback #3): Again, absolutely not. I appreciate your business and I hope to continue working together. But I can’t fulfill any request like this. Whatsoever. It’s just not. There are so many problems with this. On a personal level, just talking human to human, I don’t feel comfortable with that at all.

Levi (the retreat): So should I just go there …

Olivia: Just go! I’m gonna make you another reservation there. Go there by yourself. I’ll get you a nice table. Request that you speak to her when you get there. Try to be respectful when you go in, obviously. Don’t do anything that doesn’t go well with most women. I’m sure she’d love to go on a date with you.

Levi: What are your thoughts if I leave my Rolex behind?

Olivia: You do whatever your heart desires. If that has worked in the past, then go right ahead.

Levi: Surprisingly it has worked in the past. So maybe we will take that one back up and try it again

Olivia: You do your thing. Alright, I’ll move forward with that reservation. I’ll call concierge right now.

Levi: Alright, text me what time you can get me in.

The Art of the Pushback

Olivia offers a masterclass in pushing back tactfully and effectively. That is why I shared this video to my teenage daughter.

Several tactics that Olivia uses to win this negotiation:

1. Use “I” Statements - Olivia doesn’t say that she cannot fulfill the request. She doesn’t mention “company policy” Instead, she focuses on “I” statements, like “I am not comfortable with this request.” Levi has no way to dispute what Olivia is comfortable with.

2. Offer an alternative - Olivia is quick to come up with a new solution. In the same breath that she declines the request she comes up with an alternative: “We can make a reservation there tonight and you can ask her yourself.”

3. Coat the medicine with honey - Despite the inappropriate request, Olivia does not get personal. Instead, she reframes the request as a compliment. “Thank you for having that trust in me.” Later, she appeals to her client’s appearance and charm while refusing to agree to his request.

4. Enlist a soft ultimatum - A turning point is when Olivia says “I hope to continue working together.” Olivia frames this in the positive but signals that she is prepared to end their working relationship over this request if Levi does not respect the boundary she has set. It is at that point that he retreats.

5. Use tone of voice - Throughout the conversation, Olivia’s tone is positive and upbeat.

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Coverage of Olivia Ferney in the NYTimes and the Independent.

A scripted TV show about based on Olivia Ferney is currently in the works.

Kelly brings a wealth of outside experience to the world of technology partnerships.

Today, Kelly leads Technology Partner Programs at HubSpot and is also the co-host of a partnership podcast called Unlearn about new growth strategies. But as you’ll read below, Kelly’s perspective on partnerships has been shaped by her experiences outside of tech - in the legal and marketing realms.

Kelly is an avid reader and learner across genres and her ability to synthesize has helped make her a leading voice in technology partnerships.

I hope you enjoy this conversation with Kelly Sarabyn as much as I did …

How do you describe what you do to someone sitting next to you on a flight?

I work at a tech company forming partnerships with other tech companies so that we can win new customers together and customers can more easily use both of our products together.

How did you find your way into partnerships?

I have an unusual background. I think that’s one of the cool things about Partnerships: people come from all different journeys. For me, the throughline across my career has been reading, researching, creating ideas and strategic thinking.

Early on I worked in legal research, focused on constitutional law. And after taking some time away from work for my kids, I landed at a branding agency where I helped companies with their storytelling, their core brand message. That was my first exposure to startups and it was really exciting work. I wanted to go work at a startup so I transitioned to leading marketing at an early stage company called Pandium. And one of the key personas we sold to was partnerships teams that were building technology integrations. I interviewed customers from companies like Twilio and Square and HubSpot. One of those interviewed was with Scott Brinker at HubSpot and he later offered me a job. That is how I joined HubSpot and eventually took over our technology partnerships as a Director of Partnerships.

What trait do you look for when you’re hiring that isn’t usually on the resume?

I look for someone who is able to continually learn and actually derives pleasure from continually learning. Partnerships are incredibly complex and the market is changing faster than ever so people who are always learning are particularly well-suited to be able to successfully navigate the challenges inherent in partnerships and the broader uncertainty in the market.

What advice would you offer to someone earlier in their career that you wish someone had given you?

I’m an introvert and one thing I didn’t fully appreciate early on was how important networking is to career growth. Networking is helpful not only for landing a job. Networking is also key to understanding different roles and different career trajectories.

Can you tell me about a partnership that you’re proud of and a lesson that you carry with you from that deal?

One internal partnership I built was with our solutions partner marketing team. We collaborated together to build a partner-to-partner program called the Partner Growth Accelerator where we match a technology partner with a services partner. These partners are placed into cohorts and go through a six week training with speakers and we arm them with best practices. And then they get access to HubSpot marketing development funds (MDF). I worked hand-in-hand with Christi Williams to get this program off the ground and even though we technically report up to different functions, we were able to collaborate together to make sure that this program was a win for both our teams, for our partners and for HubSpot.

What is one thing about negotiations that you find to be true, but is often overlooked?

If you over-index on winning the negotiations that is right in front of you, you can be doing damage to the long-term relationship. I see some platforms negotiate aggressively for near-term wins but, in doing so, leave a negative impression with their partners and that has huge ramifications down the road when it is time for the next negotiation together.

What is an unpopular or contrarian view that you hold?

I think the long-tail of partners are seriously under-invested. Many companies I see focus on their top partners, they nurture and invest in those partners and then it creates a feedback loop where those partners continue to drive more and more impact. I am a big believer that, with proper systems and the right marketing strategy, long tail partners can drive a ton of value.

What is something you read or listen to that makes you smarter?

UnSiloed with Greg LeBlanc - the host is a friend of mine and he interviews people who write books across all different non-fiction genres, from biology to gender studies to politics. But it is very accessible and does not get bogged down in jargon.

Is there a book outside of business, the business genre that has been helpful to you in your career?

Revolutionary Road by Richard Yates - this is one of my favorite books. It is about people who feel they’re special, they move to suburbia and they have kids and they chafe under that. It is a book that makes you think about your values in your life and your career. We spend so many hours at work and, for me, the book made me reflect on what leaves me fulfilled in my life and in my work.

What is a question that I didn’t ask you that I should have. And what is your answer?

You did not ask what I like most about working in partnerships!

I just love how challenging partnerships are. Partnerships cross every area of the business internally, but they also require orchestration of a number of different internal and external stakeholders. You have to time that orchestration properly - if you get partners excited about working together without getting buy-in from your sales leaders, for example, then the partnership is going to fail.

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This might be the CRO. Or the CFO. Or a Board member.

Whether you know it or not, they are asking questions like …

• Why should we hire another partner manager rather than another seller?

• Aren’t we better off closing deals directly (rather than with a partner)?

The most powerful tool to address these questions is simple: partner data.

But obtaining that data is very difficult in most organizations.

There is a solution: Partner Operations.

Partner Ops is the unglamorous plumbing the powers your partner ecosystem. It is invisible when it works, but when it breaks, the ‘mess’ ends up on the CFO’s desk.

Here is how Partner Operations helps you avoid a terrible mess …

Partner Ops Powers GTM Partnerships

Partner Ops exists to turn messy ecosystem activity into undeniable board-level data. This data can vary from organization to organization but in my experience, there are the essential metrics:

Partner value metrics

• Partner attach rate: what % of deals have a partner attached?

• Partner-sourced & influenced revenue: how much revenue did partners source? How much overall revenue is with customers who use a partner (or multiple partners)?

• Partner segments - which partners are driving the most revenue?

Partner comparative metrics

• Deal size: what is the avg deal size when a partner is attached to a deal vs. not?

• Deal velocity: what is the average deal cycle when a partner is attached vs. not?

• Time-to-value: how long does it take for customers to activate or unlock product value with a partner vs. without?

Higher velocity and larger deal sizes aren’t just ‘nice-to-haves’— they are the best way to silence internal critics.

Some companies may use additional metrics to measure impact and track progress.

For example, MacKenzie Connaro, who built partner ops at LiveRamp, shared this:

“We treat partner case studies as a metric because those case studies are key to our sellers and other internal stakeholders understanding each partner’s value.

Partner Ops Also Empowers Partners with a Seamless Experience

Don’t make the mistake of thinking Partner Ops is only inward-facing.

The best Partner Operations leaders build systems - essential workflows that partners rely upon. These workflows attract partners to an ecosystem and keep them engaged.

Partner Operations is also critical to delivering a smooth experience for partners, including:

• Onboarding - clearly outlining how to become a partner (e.g. eligibility & authorizations)

• Integrations - manages clear API documentation and routing to technical support

• Co-Selling - implementing a structure for account mapping, deal registrations

• Partner enablement - a learning management system or some mechanism for delivering enablement/educational content and validating partner knowledge for badging / credentials.

• External partner metrics - data to inform QBRs, partner tiering and benefits

• Partner Benefits - access to badges, credentials, awards, and yes, payment (for resellers)

When to Hire a Partner Ops Leader

In my experience, there are three models for how to get started with Partner Ops

• Borrowed Model - this typically involves convincing the Sales Ops team to support / extend their coverage to partnerships. This can work but that person is rarely dedicated to partnerships and often gets pulled away to support sales-related work.

• Hybrid model - this is when a member of the partnerships team is responsible for both partner management AND partner operations. This is not ideal but this person is at least embedded within the team and intimately familiar with how partner realities must translate into metrics.

• Dedicated model - this is a dedicated, full-time Partner Operations leader whose job is focused almost entirely on assembling the internal metrics above and

Most partnerships teams must start with the borrowed or hybrid model and graduate to the dedicated model.

My recommendation is that by the time your organization clears 25% of revenue from partners, you need a dedicated Partner Operations leader.

My strong view is that you need to stop trying to avoid your emotions at work. That doesn’t necessarily mean you get to externalize emotions all the time. But you should think about your emotions, whether positive or negative, as information that can help you figure out how to work more productively with others.

I agree with Erika. Yet I still struggle with which emotions are fit for the workplace and which are not.

That is partly why the term “work grief” jumped out at me when I learned it last year in a post by Molly Graham, a seasoned tech executive turned coach.

In explaining work grief, Graham wrote this:

“The truth is that Work Grief is an incredibly common experience and something we need to make more space for. A major change happens — good, bad, ugly — and you need a minute to process the new reality, mourn what is in the past, and get ready to move forward.”

Failing to acknowledge the emotional toll of change at work can lead to burnout and attrition. Work grief may sound touchy-feely but it is directly tied to culture, productivity and profitability.

Examples of work grief

Work grief doesn't just stem from a layoff, as Molly Graham points out.

Grief can follow a wide range of significant changes at work.

One way to normalize work grief is to be open about it. Here are some examples of work grief from my career.

• A re-org stripped me of responsibilities I had worked for years to earn.

• A new role provided me with more scope and impact but also more stress and pressure.

• The departure of a manager whose guidance and support I had come to rely upon.

• A deal I was negotiating was signed and my relationship and role with the partner changed.

• A promotion I thought I had earned was turned down for reasons I didn’t agree with.

What makes work grief difficult?

There is no comparing the grief that comes from change at work with personal challenges like disease, divorce, death, addiction, bankruptcy, arrest, etc.

Work grief is a kind of privilege at a time when so many talented people are under-employed and unemployed.

But acknowledging work grief does not require comparison.

Grief is grief. And it comes in different forms.

What can you do about work grief?

Here are three ways you can help yourself and others through work grief:

• Acknowledge the change at work - When you know someone at work who is going through a big change at work, especially a setback, reach out to them. Ask them how they’re doing. And listen. This could mean getting lunch or simply an email or Slack message. It doesn’t need to be a large time investment. If you are a people leader, give your team a chance to share how they are feeling the change. Even a small gesture 1:1 or a few minutes during a team meeting can go a long way.

• Build your identity outside of your work - Work grief cuts way deeper when your entire sense of self is tied to your work. Over a forty year career, a major setback (or a few) is almost inevitable. To avoid severe work grief, make time to be a human outside of work. Find a hobby. Join a team. Volunteer. Your life is more than your job.

• Invest in trusted relationships - I think of emotions like gas. I can try to keep them inside, but eventually I’ll become like a shaken soda can. There is no better release than opening up to people I trust. I think this is true for most people. Trusted confidants are possibly the best antidote to work grief. Since relationships require time and space, this means setting aside time for the people you care about. Make time to take a walk with a friend. Call a parent or sibling. Consider a professional coach or a therapist as a way to strengthen your relationship with yourself.

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One Ask & One Offer

New Years Day comes with a couple annual traditions here at TfT:

• An ask: what is a topic you want TfT to cover in 2026? What is a deal dilemma or partnership puzzle you’re facing? Who do you want to see interviewed? Please reply to this post with what you want from This for That in 2026.

• An offer - I typically begin the year with a reflective or inspirational January 1st post. If you are looking for something more uplifting, check-out these posts from the archive:

  • 2022: Craft Your Character This Year

  • 2023: How Will You Fail This Year?

  • 2024: This Year, Find Your Inner Kariko

Ross Siegel can do something similar with people from across his personal and professional network:

• Who do you that holds multiple patents and works in fintech?

• Who do you know that attended Davos before 2015?

• Who do you know with expertise in European trucking logistics?

Ross has as vast a network as anyone I know. Like the very best connectors, he nurtures relationships with ease but also with intention.

He has a sharp wit and deep insight from his experiences at big companies (Yahoo, Apple, Fox Interactive), startups (Meebo,Pulse, DataLogix) and as a founder (Jobolous).

I hope you enjoy this conversation with Ross Siegel.

Tell me about yourself

I would like to be a Californian, where I lived for half my life, but I’m often mistaken for a New

Yorker, because that is where I’ve lived the other half of my life … and live today.

I work at the nexus of media, marketing and technology. And if you had asked me when I was 16 years old what I wanted to do when I grow-up, I would have said some version of that. The path I’ve taken has been very circuitous and different than what I set out to do. I never really had a plan. But that has worked out really well for me.

How do you describe your job to someone on a flight who asks you, what do you do?

I work for a boutique management consulting firm called MediaLink at the nexus of media marketing and technology. Our firm is considered one of the best at what we do. Our firm is owned by an agency called United Talent Agency, which is one of the three big Hollywood talent agencies.

What is an unpopular or contrarian view that you hold?

It is not the best product but the best story that wins.

Apple does not always have the best product in every market but Apple marketing fundamentally understands that sleekness and ease of use are more powerful than the technical specs inside the hardware. That is the story Apple tells.

Taylor Swift’s music is not better than other musicians. I find her music to be vanilla and boring. But what she’s done is create a wonderful story. And she makes her audience feel part of her story. She is exceptionally good at using media to tell a story with and for her audience.

What is one thing about negotiations that you find to be true but is largely overlooked?

The first thing is you have to realize that you may not be as good a negotiator as you think you are. Many people like to think they are tough and really good at negotiating … but most people are not.

I’m not a very good negotiator. I’m impatient during negotiations. I have learned that is my weakness. I’ve also learned, despite that weakness, I am good at converting prospects into clients because I’m good at building relationships. And a strong relationship counts for a lot during a negotiation.

Tell me about a partnership that you’re proud of and a lesson you carry with you from that deal.

I’m going to share a deal that I learned a lot from but I wouldn’t say I’m necessarily proud of.

I was leading Business Development for Yahoo! Small Business in 2010 when Yahoo! was one of the biggest companies in America. Anyone at Yahoo! who had an RFP related to small business came to me. And one day a sales leader came to me with a $50,000 RFP from AMEX. This was not a huge opportunity. But I said to the salesperson “I think we can make this much bigger by expanding the scope to reach across all of Yahoo.” He and I set out to do that and things got a messy and chaotic internally. This deal did turn into one of the biggest deals for Yahoo! that year but it was not pretty.

I learned so much from that deal about the importance of enlisting help from others. Candidly, I didn’t know what I was doing and I didn’t have the confidence to ask for help.

What advice would you offer to someone earlier in their career that you wish someone had given to you?

Be patient. It is more important to build relationships,develop expertise,absorb, and generate a reputation among colleagues and clients. If you stick around somewhere and become known as someone who is good, you’ll be better off than if you hop around in search of better roles and companies. Ultimately it’s what you do that matters, not the organization at which you do it (though that doesn’t hurt)

What is something you read or listen to that makes you smarter?

“On the Media,” the NPR podcast, has given me this incredible critical thinking method that allows me to think about what is the real motivation. I’m able to take situations in my life and reflect on “what am I hearing from this person? And what are they really telling me?” That podcast is exceptional at digging into what is the real story underneath the surface.

What is a book that changed your perspective?

“The Great Crash of 1929” by John Kenneth Galbraith. And, believe it or not, it is about the great crash of 1929. Reading that book you could change the names from 1929 to 2007 and it would be nearly the same story. There is a chapter called “In Goldman Sachs We Trust” … in this book from 1929.

That book taught me to have a healthy ingredient of skepticism.

What is a question I didn’t ask you that I should have?

You could have asked me “How would can a startup compete against giant platforms today?”

I would have told you that small companies today need to either have some deep insight that is wildly different from everyone else or they need to provide something that big platforms depend on.

For example, the Trade Desk had an insight that was different than everyone else - they understood that ad agencies controlled so much media spend. Nearly all the adtech platforms tried to go to brands directly while The Trade Desk catered to ad agencies. So The Trade Desk built their whole business around serving ad agencies.

Alternatively, a company like DoubleVerify understood that Google and Facebook need an independent company to verify their ads.

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If you’re new to This for That, The Grinding Wheel is a semi-regular series of curated recommendations to help make you sharper … or just have fun.

For the sake of quality, I limit the frequency of these recommendation posts … the last was over a year ago.

I hope you enjoy the recommendations below and can use them this holiday season.

As always, please share with me what you suggest I read / watched / listened to.

To Watch

• A movie for the whole family: Billy and Molly - this documentary is the true-story of the friendship that forms between a man in rural Ireland and the otter that visits him daily. I don’t use words like “beautiful” or “heart-warming” very often but this film is both. (77 mins, Disney+ or National Geographic’s YouTube channel).

• A political thriller that keeps you on the edge of your seat: House of Dynamite - the United States we will have less than 20 minutes to respond if a foreign enemy sends a nuclear missile our way. This film depicts those 20 minutes from a few different perspectives. It is unsettling but also hard to stop watching … and it serves as a reminder of the importance of global partnerships (112 mins, Netflix).

To Read

• A fun coming-of-age story (fiction): The Extraordinary Life of Sam Hell - this is the story of a kid born with red pupils, the challenges that abnormality creates for him and how he overcomes them. I loved this book. It will resonate with anyone who ever felt different as a kid (a.k.a everyone) and anyone who needs a distraction from life as an adult (a.k.a everyone).

• A fascinating coming-of-age story about two giants: Apple in China (non-fiction) - Patrick McGee tells two stories at once - how Apple and China used each other to grow into modern-day powerhouses. He tells these two macro stories with micro details - introducing characters and scenes from inside Apple and China. The book is a bit heavy on the details of manufacturing electronics but I came away with such a clearer understanding of both Apple and China.

To Listen

• A conversation about re-inventing yourself in the face of a health crisis - this interview with Jessica Slice opened my mind about what it means to be disabled. I was so inspired by Slice’s ability to reframe change as opportunity. Host Maya Shankar is warm and curious as always (A Change of Plans podcast).

• A deep dive into being different: Trader Joe’s - Trader Joe’s operates by its own rules. That is one reason I love shopping there. A 3-hour deep dive into the history and strategy of a grocery store may not sound enticing at first but the time flew by and I learned so much (The Acquired podcast).

To Eat

In the spirit of that bullet, here are a couple of my favorites from Trader Joe’s:

• Korean Beefless Bulgogi - defrost this, add rice + Trader Joe’s Soyaki + a touch of sriracha for an easy and tasty meal that is healthy and less than $10.

• Dark Chocolate Peanut Butter Cups - Nothing satisfies my sweet tooth as efficiently. Just one or two (okay, three) and I’m all set. Better tasting than Reese’s Pieces Cups. Cheaper than Unreal Butter Cups.

For Work

• A better work-from-home experience - my Costco standing desk makes me happy to get off my ass when I work from home. It is easy to adjust and I especially like the glass top where I jot notes on with a dry-erase pen on during meetings. At under $300, it is less than most other other standing desks. Look for the Tresanti brand.

• A better 1:1 meeting experience - my view is that one-on-one meetings should either be outdoor, walking meetings (when in-person) or on the phone (when not in-person). For remote 1:1 meetings, invest in a solid noise-cancelling, wireless headset to immerse yourself in the conversation and still have the freedom to walk around. I like my Beats headphones. I’ve also had success with Logitech. I don’t believe you need to spend more than $250.

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We draft a joint business plan together. We align on revenue projections. We agree to start mapping the customers we will pursue together.

My CEO’s mouth is watering at this burgeoning global alliance that I’m forging.

Then, the Managing Director at this GSI informs us that we need to pay their firm $250,000 to train their teams to use our software. Some partnership.

Next, they send us an 80-page contract to sign that makes it clear that their senior team, who we have been working with for 6 months, does not understand our product.

As this partnership goes up in flames, I am distraught. As I reflect on this debacle, I vow not to make this mistake again.

That is how I became a raging advocate for minimum viable partnerships.

Minimum viable products … learning before scaling.

Twenty years ago the notion of a minimal viable product was fresh.

Today, minimum viable product (MVP) is a universally accepted approach to product development among startup founders and investors, thanks in large part to Eric Ries and Steve Blank.

Famous startups MVP stories include …

• Dropbox started with no product, just a 2 minute video that generated 75,000 sign-ups. Today, Dropbox is valued at $10B.

• Airbnb started when its founders rented out one air mattress to attendees at a design conference. Today, Airbnb’s valuation is $75B.

• Uber started as a simple text-messaging service in one city. Today, Uber is worth $200B.

Minimum viable product is about gathering customer feedback before a writing business plan, assembling a team or pitching investors, etc.

Applying the MVP playbook to partnership

Minimum viable partnerships are a first cousin of minimum viable products. The goal is the same for both: learn as much as possible with the least amount of effort and investment. Then, use those learnings to iterate and refine.

Here is what minimum viable partnerships look like:

• Before you publish a press release touting your new partnership, build a proof-of-concept and collect feedback from 10 customers.

• Before you go on stage at an industry conference to announce a partnership, prove that a customer wants to use your joint solution.

• Before you craft a co-selling and co-marketing plan together, see if you can close a few deals together.

Minimum viable partnerships are about having the discipline and patience to listen to customers before announcing what a game-changing partnership you’ve struck.

MVPs are key to co-selling

Co-selling is very popular in B2B software right now for good reason. With co-selling, each partner builds a direct relationship with the same customer. Unlike reselling, co-selling partners each negotiate their own agreement (and pricing) with the customer in parallel.

Co-sellling is when Microsoft and Salesforce team up to convince a customer to transition off HubSpot. Or when Shopify and Stripe partner to win a retailer’s RFP.

But co-selling is much harder than it sounds. Selling a bundle of complimentary goods is more complex than selling a single product. Co-selling requires that the customer makes two buying decisions at once - no small feat!

Successful co-selling requires a compelling “better together” story that the customer can grasp quickly.

That is why minimum viable partnerships are so important.

Without validating your “better together” story with actual customers, you have no idea if you are putting together a strategic partnership or a waste of time.

I learned the hard way. It was agony.

Make sure first step with your next partnership starts with customer feedback.

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More reading

• The Lean Startup, Eric Ries

My recent conversation with Erika Wool, who leads Product Partnerships & Strategic Partnerships at Stripe, took place during her second maternity leave, which I had not realized when I reached out to her.

I knew from past conversations with Erika that she brings an insightful perspective on building businesses, partnerships and more. But I was struck how being at home with her family - and away from the daily rush of product reviews and partner pitches - gave Erika the space to be reflective.

I hope you appreciate Erika’s perspective as much as I did.

Tell us about yourself.

The answer to the question is really shifting for me. Being 10 weeks into my second maternity leave, I’m realizing that I want to define myself differently than where I work, where I’m from or where I live. I want to define myself by my relationships with my family and also things that matter to me as an individual. I get a lot of meaning from work, so that will always be a component of my answer … but I want who I am to be about more than work.

Basically, I’m rewriting my answer to this question. I would guess the same is true for a lot of your readers, especially those in the midst of some kind of life transition.

How would you describe your company and your role to someone sitting next to you on a flight?

I like the way this question is phrased but personally I find that the people I have to explain my role to most often are colleagues internally, not people I meet externally. Partnerships mean different things at different companies. Oftentimes I encounter folks at Stripe who haven’t worked closely with partnerships as a function, so I have tailored my description of my role to how I try to explain this to them.

At Stripe, we define everything we do by our mission - we build economic infrastructure for the internet - and the thing that makes it economic are all the partnerships we have in place. Stripe is not a card network. Stripe is not a bank. Stripe is not a payment method. So if we want to provide economic tools to the businesses that build on Stripe, then we need partnerships. That is what we do on Stripe’s partnerships team.

What is an unpopular or contrarian view you hold?

My strong view is that you need to stop trying to avoid your emotions at work. That doesn’t necessarily mean you get to externalize emotions all the time. But you should think about your emotions, whether positive or negative, as information that can help you figure out how to work more productively with others or create new insights about problems you’re tackling. When you’re putting energy into suppressing an emotion that arises from working with someone else or working on something, that is standing in your way. I think we all stand to benefit by figuring how to use our emotions at work more productively.

Tell me about a partnership that you’re proud of and a lesson you carry with you today from that deal.

One deal that I am particularly proud of was when Stripe was chosen to be Apple’s first launch partner for Tap to Pay on iPhone. It was exciting to shape the product that Apple ultimately launched and built. That deal really solidified to many people that Stripe can be a competitor not just in online payments but also in in-person payments and drive innovation in a category that we were previously an afterthought in.

I started working on this opportunity as soon as I started at Stripe in 2019. My very first meeting with Apple was about our interest in turning iPhones into payment terminals.

This deal taught me that you just have to get started. I obviously wasn’t super deep on Stripe’s products yet. I didn’t know that much about in-person payments, which is wildly complicated. I didn’t know that much about hardware yet. But that didn’t prevent me from being a good partner externally or internally. I had to be mindful and upfront about what I didn’t know. But I was still able to lead and turn the opportunity into a tangible deal to be done and then work with our cross-functional team to pull off a great launch.

What is one insight that is core to how you approach relationships and build partnerships?

Don’t forget that there’s like a human on the other side of the table. Make zero assumptions about what matters to that person and what success looks like for them. Even if you don’t have a lot of time, ask questions - especially at moments where you think you know what someone means but haven’t heard it directly from them.

What is one thing you have found to be true about negotiations but is often overlooked?

There are many, many ways to create value and the sooner you get past negotiating for the same pieces of value, the more productive the deal is going to be. It is very rare in my experience that two companies negotiating a partnership agreement care about exactly the same two terms or outcomes equally.

What advice would you offer to someone earlier in their career that you wish someone had given you?

Don’t overthink it. I think that the partnerships function tends to attract really thoughtful people but we can often overthink things. Whether you’re talking yourself out of doing something or, conversely, sticking with doing something. I talk to so many people who think their career need to be linear and they put so much pressure on each step along the way. And that pressure can lead to overthinking. Sometimes you have to just give something a try and see how it goes.

What is something you read or listen to that makes you smarter?

• Anything that Molly Graham writes - she is really thoughtful about some of the topics that we touched on here, like managing and how to make decisions about your career and her work just makes me smarter about how to be a person in a company.

• When it comes to AI, I read Every’s newsletter. I want to learn how to build with AI versus just leveraging it for productivity and Every focuses on tools and how to use them, and I have found that to be really helpful.

What is a book that has changed your perspective?

There was a moment in my career where I was experiencing severe burnout and I was having trouble connecting with the parts of me that fuel me at work, specifically my curiosity. I happened to read Sapiens by Yuval Noah Harari years after it was originally popular and it re-ignited my sense of curiosity about the world. I thought to myself, “holy shit, humanity could have done literally anything and this is what we chose to create.” This really helped me find a way to reframe. And even years later, when I feel like I’m hitting a wall personally or professionally, I remind myself of that perspective and how I felt when I read that.

What is one question I should ask you that I didn’t?

When it comes to work, what is something that you think matters now that you didn’t realize mattered before?

My answer is that, before I went out on my first parental leave I had been leading teams for a long time and have had a lot of people go out on leave - be it some kind of parental or caregiver leave - and I always thought I was empathetic and took pride in thinking “I’m a good manager for someone at these big transitions in this life.” And I think I’ve realized that, after returning from my first leave and experiencing first hand what that’s like, that I could improve some things.

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This is one of the most important questions not only for artists but for anyone pursuing a craft or a career.

I have struggled with depth versus breadth questions throughout my career:

• Should I stay in this role to refine these skills or take on a new one?

• Do I remain at this company or industry or leave for that one?

Grappling with this question led me to a simple framework for evaluating the trade-offs.

A career framework for depth versus breadth

My process starts with two basic questions:

• What industry do I want to get experience in?

• What functional role do I want to get experience in? (e.g. partnerships, operations, etc.)

Here’s how I chart depth versus breadth options:

I started out as a generalist with some basic skills but not much depth in any domain. Over time, I had to decide whether to pursue becoming:

• Industry and Functional Specialist - This is the sales lead, for example, who has sold to retailers for many years. She knows every persona within a retail organization and how they make decisions.

• Industry Specialist - This is the fintech specialist who has worked in operations, marketing, customer success and partnerships. His versatility throughout the fintech industry is a powerful strength; his functional knowledge is more shallow.

• Functional Specialist - This is the partnership dealmaker who can structure agreements with every partner type and has led deals across each customer segment in several multiple industries.

I don’t know which path is right for you. But here are a few things I have learned along my journey:

Breadth is your asset in a changing economy.

If there is one safe bet today, it is that the jobs will look very different in 10 years (or likely much sooner). Given this, I find it is risky to specialize over the long-term in one industry and one function.

In David Epstein’s book Range, he makes a compelling case that developing deep expertise in a silo, a single domain, is problematic. Citing evidence from sports, science and art, Epstein highlights the power of developing knowledge in one domain and then transferring it to another.

Personally, I owe much of my effectiveness in one domain (technology sales & partnerships) to the knowledge I transferred from the years I spent in another domain (political communications).

Breadth (also known as “range” or “versatility”) is particularly valuable in an era of artificial intelligence. As David Epstein writes:

“The more constrained and repetitive a challenge, the more likely it will be automated, while great rewards will accrue to those who can take conceptual knowledge from one problem or domain and apply it in an entirely new one.”

Zig-zag from here to there.

Over the years, I have cultivated experience in one industry and used that experience to create a new opportunity, where I gained new functional expertise. Then I used that functional expertise to gain a foothold in a new industry. By zig-zagging between a few industries and functions, I have gained depth and breadth.

I liken this to the way that monkeys move through a canopy. They use one arm to cling to what is familiar (the branch behind them) and another arm to reach for the next new branch.

Most careers are not linear. Zig-zagging with intention is often the way to acquire a valuable breadth and depth of experience.

Be married to the problem.

I once heard a gem of career wisdom from the entrepreneur Suhail Doshi that stuck with me: “Be married to the problem, not the technology.” This advice applies to everyone, no matter what you are pursuing. Don’t get distracted by shiny objects - cool tech, hot companies or a fancy title. Be married to the problem.

Building something meaningful - a product, a team, a career - is so difficult. But if you are truly committed to addressing the underlying problem, then you can find the strength to push forward through the setbacks you will inevitably face.

Once you find a problem you are truly committed to, the next question is how can you help solve that problem. The answer lies in honing your skillset …

Focus on the craft.

Even though I work at a desk most of the day, I try to approach my skills like a woodworker or a chef treats their knife. I'm obsessed with sharpening my blade, refining my skills so that I can cut with precision through obstacles at work.

This craftsman mindset is captured in the excellent documentary Jiro Dreams of Sushi, about a master sushi named Jiro Ono in Tokyo. During the film the 85 year-old chef describes his attitude towards his craft:

“Once you decide on your occupation... you must immerse yourself in your work. You have to fall in love with your work. Never complain about your job. You must dedicate your life to mastering your skill. That's the secret of success.”

While I’m certainly guilty of complaining about my job, I find inspiration in Jiro Ono’s lifelong pursuit of the skills needed create the perfect piece of sushi. Check out the film.

Listen to your own voice.

You will have colleagues, friends, parents and others who will insist that you need to focus on depth - that you should stay put and gain more expertise in your current position. You will have others you trust who will argue for breadth - that your growth requires that you transition into something new. These breadth versus depth dilemmas can be difficult. But you cannot let others’ opinions define your career decisions.

You need to chart your own path and listen to your internal voice about how long to stay and when it is time to move on. As former Intel CEO Andy Grove once said:

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Sunil began his career as a lawyer and his work in technology started with crafting tech policy at the Federal Communications Commission (FCC). His expertise in communications policy helped Sunil land business development roles at Yahoo! and Google. Since then, Sunil has helped build new businesses in on-demand logistics (Uber), digital assets (ABRA), and now as a co-founder at SiftAI, which develops AI agents that solve problems for social customer support and community teams.

I once had a conversation with Sunil during a chapter of his career when he was consulting and he shared a perspective that I’ve never forgotten. Sunil told me “I view these consulting projects like paid interviews. I’m getting paid by these companies to understand the people and the problems they’re facing and I then get to decide if I want to continue working with them.”

It is gems of wisdom like that led me to this conversation with Sunil. I hope you enjoy it as much as I did.

Tell us about yourself

I’m a curious soul that is constantly learning. I have a deep insecurity for mediocrity. I have a lot of confidence in my ability to impact the world positively, which also causes tension and stress if I'm not achieving that. That can also be a curse. When you're never really satisfied, you're always thinking about doing something else, you don't smell the roses along the way.

Lastly, I am blessed with a community of many friends and family.

How would you describe your company and your role to someone sitting next to you on a flight?

My answer reflects my approach to doing deals: how I describe what I do depends on who I’m talking to. I have a different answer depending on whether the other person works in technology or not … and based on how old they are. So, before I say anything about my company, I ask the person questions to understand who they are and what they care about.

I’ve worked on numerous different technologies over the years, but the common denominator is taking new technologies and bringing them to market to solve problems that very often people don’t realize they have.

What is an unpopular or contrarian view you hold?

Well, the Russians defeated the Nazis. I think many historical narratives tend to overdramatize the role of the United States in history. There’s no question when you read the history that the Nazis were more defeated by the Russians, but the narrative of WWII is often very different than that. I find that the popular narrative can be completely wrong, not because of differing opinions, but because of political reasons. The best phrase that comes to mind: “history is written by the victors”. For me, the way I get to the truth is by reading and listening to different media with contrasting viewpoints.

Tell me about a partnership that you're proud of and a lesson you carry with you today from that deal.

I really loved a deal I worked on where we brought Google WiFi to Starbucks stores, the first time Google got into the access business in a mass market scale. While that specific product no longer exists, Google has significantly grown its investment in Fiber and access since that deal. It was a thrill to bring connectivity to some of the most remote parts of the world, and knowing that I had a small part in that.

I had done all my homework, read all the 10-Qs. This was before ChatGPT. I knew deal economics. I know the legal elements - it helps to have a legal degree. I knew all the arguments for and against the deal.

And there was a point during the internal deal review meeting where I outlined why we should do the deal, and at the end, I said, “look, if we don’t win this RFP, you guys can fire me.” The beauty of that was that my leadership was not going to fire me. But it showed how much conviction I had that this was the right opportunity for us to take.

What is one insight that is core to how you approach relationships and build partnerships?

Empathy - that's really it. What is the other side worried about? What are they worried about that they shouldn’t be? What are they not worried about that they should be? The objective is to get to the underlying core assumptions of the negotiation.

What is one thing you have found to be true about negotiations but is often overlooked?

Empathy starts with listening. Oftentimes, people are just waiting for their turn to talk get their point across.

Another is context, you have to separate the internal negotiations from the external negotiations. The hardest challenges I’ve faced on deals are often internal negotiations. And you need to have situational awareness to switch between the realities of your partner’s organization versus your own organization.

What advice would you offer to someone earlier in their career that you wish someone had given you?

Coming from a household of doctors, I was instilled with a sense that if you do good work, it will speak for itself. And that is true … but it is not the full truth. If I could go back, I would have invested in stocks earlier.

I wish I had a better understanding of the distinction between labor and capital.

Work is not all about the money but it does matter. And until you reach the upper echelons of management, you’re in the labor world. If I had put more time and attention into capital wealth creation, it would have been better for me overall.

What is something you read or listen to that makes you smarter?

I try to find contrasting views even if it is painful. Doing so helps me to learn and grow by testing my assumptions.

I really believe in reading longform books. Making time to step away from my inbox and getting into a mindset of absorbing new information. I personally prefer the printed word on paper. I also find it important to read different genres and disciplines - technology, history, religion, etc.

What is a book that has changed your perspective?

Technological Republic, Alex Karp

Winners Take All, Anand Giridharadas

The Post-American World, Fareed Zakaria

What is one question I should ask you that I didn’t?

How does AI change business development? In my mind, there are a couple ways that I’ve integrated AI into how I operate …

1. Legal - I use AI to assess legal risk.

2. Research - has this company done these types of deals before? It is malfeasance if you aren’t reviewing their 10-Qs and 10-Ks. I used to read them manually. And now I just use AI to do that. I also find executive interviews on YouTube and use AI to summarize those interviews.

I also play different AIs off of each other. I’ll get an answer from ChatGPT and I’ll copy/paste it into Grok and tell Grok “I just got this answer from ChatGPT, I know you can do better. Show me.” It works.

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The first person to respond was a generous stranger in Ireland …

Hugh Durkin had no reason to share his hard earned knowledge with me. But he did.

We scheduled a call and Hugh shared insights he had gained from the partnership roles he had held at Facebook, HubSpot, Intercom and Zalando.

Hugh’s willingness to share his wisdom - while running his own startup - reminded me that the greatest thing about the internet is how it connects like-minded strangers from across the globe.

I started writing This for That in late 2020 because I wanted to connect with others about the craft of building partnerships … but I couldn’t find much at all on the topic online.

That is why I was excited to recently learn that Hugh started a newsletter - Platform Partnerships. Hugh brings the rare perspective of someone who can switch seamlessly between founder and operator, seller and engineer - he is a 3x company founder and 3x partnership leader at publicly-traded companies.

Today, I’m sharing a post from Hugh’s newsletter because I found it useful and I think you may also.

If you work in partnerships and you haven’t heard talk recently about MCP, then you soon will. And hopefully Hugh’s post below will help you.

I’ve also included some additional links at the bottom with more coverage of MCP, in case you want to dig deeper.

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An MCP Primer for Platform Partnerships Teams

By Hugh Durkin from Platform Partnerships

If you’re managing platform partnerships, you’ve probably already heard about MCP (Model Context Protocol). You’ve also probably wondered what impact it might have on your strategy, partnerships, and day-to-day. So I thought it might be helpful to break down what MCP is, what it isn’t, and what it could mean for partnership leaders.

What MCP is

MCP is Anthropic’s relatively new open standard that lets AI assistants like Claude and ChatGPT connect to external sources of context.

Think of it as a standardized way for AI systems to “talk to” your existing data and artefacts without requiring custom integration work for every AI interface.

Instead of building separate integrations for Claude, ChatGPT, and every other AI assistant out there, platforms (or third-party developers) build MCP servers that work with all of them. It’s like a universal adapter - similar to USB - for AI platforms.

MCP servers typically expose three types of capabilities:

• “Tools” - functions the AI can call (example: HubSpot’s “create_contact” or Linear’s “create_issue”)

• “Resources” - data the AI can read (example: SQL databases, GitHub repository files)

• “Prompts” - templates that help the AI interact effectively (example: “Generate a sales email using this contact's interaction history”)

“Tools” are typically the most used capabilities, and typically interact with existing platform APIs to search, read, write, enrich and change data.

“MCP” is to AI assistants as “integration” is to business software

Adoption of MCP is growing fast. Launched in November 2024, there are already thousands of MCP servers listed in directories like Glama, MCP.so, and Composio.

Major platforms like GitHub and HubSpot recently released their own MCP servers.

Even OpenAI - an Anthropic competitor - adopted the MCP protocol across their products, in part because the broader ecosystem benefits of a standardized protocol outweighed the competitive risks of adopting a rival’s standard.

What MCP isn't

MCP isn’t a magic solution to a lack of API coverage or extensibility. It is - for now at least - essentially a standardized wrapper around existing platform APIs. If your platform doesn’t expose data or actions you need via API, MCP might not be able to access them in a structured, reliable way either.

“Tools” for searching and browsing websites are available to MCP, but this type of unstructured data is often slower to access and harder to predict the availability of.

So MCP won't solve your API coverage gaps, but it will make them more visible to customers expecting strong integrations with AI products and features. As more customers rely on AI assistants as their primary interface, they’ll naturally demand the ability to interact with more data in more systems.

MCP also isn’t a replacement for existing integrations and partners. If anything, it augments them and opens them up to more use cases. It's like a new distribution channel that works alongside your existing partner ecosystem, not instead of it.

The ISV opportunity

For ISVs and SaaS platforms, MCP offers new ways to make their products “AI-native” quickly. A project management tool integrated through an MCP server suddenly becomes accessible to every AI assistant, potentially reaching millions of new users.

HubSpot recently launched the first CRM deep research connector with ChatGPT, enabling sales teams to analyze customer data and identify new opportunities using natural language within ChatGPT. Linear created MCP servers so AI assistants can create tickets, update project status, and manage development workflows directly.

The near-term opportunity is the creation of additional utility value for customers. Which creates incremental distribution value for ISVs and platforms. Getting your product embedded where users increasingly spend their time is a win for everyone.

The MCP advantage for AI platforms

Glama already offers access to over 2,300 “remote capable” MCP servers

There are obviously benefits for AI platforms like Anthropic and OpenAI, too. MCP solves a critical limitation - AI assistants perform best when they can interact with and act on real business data and perform real business actions.

Just in the past few months, MCP servers have been launched by:

• CRMs (like Salesforce and HubSpot), enabling AI assistants to interact or create customer data and automation flows

• E-commerce platforms (like Shopify and BigCommerce), enabling AI assistants to automate inventory and order management

• HRIS systems (like Workday and BambooHR), enabling AI assistants to interact with and analyze employee data

By connecting to enterprise systems of record, AI assistants start to generate tangible productivity gains quickly. When Claude can create Salesforce opportunities, update HubSpot contacts, or process Shopify orders through MCP connections, it transforms these interfaces from chatbots into business automation platforms in their own right.

The integration acceleration effect

Here’s where MCP gets interesting for partnerships teams: it can accelerate the development of AI capabilities across partner products - and your own.

Historically, new integration development followed a predictable pattern. Customers request integrations, partners request APIs to build them, product teams add these requests to a backlog, and - often months or quarters later - the integration exists.

MCP changes this dynamic because fast AI platform adoption creates immediate market pressure.

When every user of every AI assistant expects the products and platforms they already use to integrate with them, API development - for AI use cases - gets prioritized. When competitors quickly launch comprehensive MCP servers, internal debates about prioritizing API coverage and extensibility get resolved quickly.

We’re seeing this play out in real-time.

Platforms that historically had limited extensibility and API coverage are expanding their programmatic surfaces quickly - specifically to support AI integration use cases.

What this could mean for platform partnerships

If you’re managing partnerships for B2B software products and platforms, MCP creates opportunities and requirements.

The opportunities are the ability to create utility value for customers - and the ability to create new distribution value - through AI assistants and platforms.

The requirements are platform and product changes required to ensure your products remain relevant as AI assistants become a primary interface in the world of work.

MCP adoption timelines are compressed compared to previous platform waves. Companies leaning into AI assistant integrations - through MCP - will enjoy significant ecosystem advantages as AI assistant usage grows.

Integration patterns we’ve seen before - where fully integrated customers retain better, and expand faster - are about to repeat at unprecedented speed and scale.

More resources on MCP

• Lenny’s Newsletter: An AI Glossary

• Hardcore Software by Steven Sinofsky: MCP - It's Hot, But Will It Win?

• Software Synthesis: Model Context Protocol: AI's TCP/IP

• Technically: Why Is This MCP Thing Everywhere

I’ve turned to Rishita for advice in the past so I wanted to share her perspective with you here…

Tell us about yourself?

I’m a mom of two. A techie. I was born and raised a Texan and developed the mindset of a San Franciscan (10+ years) but I am really a New Yorker at my core. So I moved back to NYC last year and it has been great.

How would you describe your company and your role if we were sitting next to each other on a flight?

Describing my job is always a fun exercise, and I often resort to “I close deals between companies, but I’m not a lawyer” (much to my parent’s disappointment). I’ve spent the last 15+ years across consulting (Deloitte S&O) and tech (Google, Amazon, Adobe) building partnerships and scaling products and I’m now stepping into a leadership role at CrunchLabs, an educational STEM toy company created by Mark Rober, a NASA engineer turned creator. This opportunity is one of a kind - I’ll get to bridge my domain experience - BD, retail, tech, and education - and apply what I have learned to an an organization with a fantastic mission focused on helping kids get excited about learning.

What is an unpopular or contrarian view you hold?

Too often I see high-growth companies turn to advertising as their next “new business venture.” Instead of doing the hard work required to understand their customer’s real willingness to pay, they default to standard monetization models. While this may boost profits in the short term, it is a race to the bottom for CPMs and doesn’t build CLV (customer lifetime value).

Tell me about a partnership that you are proud of and a lesson you carry with you today from that deal.

I co-led a deal with Disney to bring Frozen voices to the Google Assistant. I learned that you get one opportunity to walk away from a partner during a negotiation. In this particular instance, an accidental hit of the “end call” button instead of “unmute” was the perfect antidote to the rising tensions on the call. Taking a 10 minute break in a live negotiation may actually be the fastest route to alignment (pro-tip: this also works with children under five).

There is one opportunity in every deal where you can issue an ultimatum or threaten to walk away. It can be really effective to draw that hard line. It shows where you will not budge. But you need to choose that issue and pick that moment carefully.

What is an insight that is core to how you approach relationships and build partnerships?

Be genuinely good as much as possible, but at all times, be genuine.

What is one thing you have found to be true about negotiations but is often overlooked?

Most people overlook how much homework is involved in getting a deal done. People tend to think of the cool or sexy aspects of BD and partnerships - the negotiations and networking. In reality, there is so much background that goes into a deal - evaluating the partner landscape, building a business model, understanding the internal and external stakeholders, tracking progress, and holding everyone accountable to actual milestones - that is where the real work is.

What advice would you offer to someone early in their career that you wish someone had given you?

Your greatest asset is the cross-functional people you work with.

What do you read or listen to that makes you smarter?

How I Built This (podcast) - these episodes get into the actual grit and day-to-day work of creating a new business. It it refreshing to hear about the process of “figuring it out” versus just the glory of the growth phase.

What is a book that changed your perspective?

The Power of Habit by Charles Duhigg. It only takes 21 days to form a habit. Keeping that knowledge tucked away has made every new challenge less intimidating - I became a runner, finally start flossing 2x a day, and learned to love to cook.

Later that day, I lose patience with a different colleague’s endless small talk when I just need a quick answer.

Can you relate?

Then you are familiar with two fundamental personality types:

• Relational people invest in building relationships even when there is no immediate payoff. They view getting to know others as valuable in itself.

• Transactional people focus on extracting specific information to accomplish their goals and view relationship-building as secondary.

Neither approach is inherently better. The most effective people adapt their style to the situation and the person they are working with. But when you are trying to get a deal done with someone whose style differs from your own, tension is inevitable.

Here's how to recognize these different approaches and navigate the friction they can create.

Relational people & behaviors

My friend Aaron Verstraete collects relationships the way some kids collect seashells on the beach.

Aaron can tell you an interesting nugget about nearly everyone he works with: Paul in Marketing was featured in People magazine; Sasha in Operations was a pro tennis player, Mike in Finance won a Super Bowl ring, etc.

Like a squirrel, Aaron stores these nuggets of information and makes use of them when he spots the opportunity.

In conversations, relational people like Aaron tend to ask open-ended questions and they actively listen to the answers. They volunteer personal information about themselves and, in doing so, invite others to do the same. They create a sense of connection with others.

If relational people had a mascot, it might be Ted Lasso. In a memorable scene during season 1, Ted shares his outlook: “For me success is not about the wins and losses, it is about helping these young fellas be the best version of themselves on and off the field.”

Transactional people & behaviors

Compare Aaron with my more transactional friend. Let’s call him Rob. You likely know a Rob. You may know several.

When Rob calls or texts, it is typically because he needs something - an introduction, a job referral or a donation.

Highly-transactional people, like Rob, tend to view relationships through the lens of cost-benefit analysis. In conversations, they get right down to business. They listen to extract specific information of use to them.

If transactional people had a mascot it might be Gordon Gecko from Wall Street. In the film, Gordon is a cut-throat investor who says “If you need a friend, get a dog.”

Why most people are both

Rob may sound like an ass. And Aaron like an angel. But it is not that simple.

Aaron can be transactional in certain circumstances. We all can. And there are situations where Rob is highly-relational. Also, it is inaccurate to suggest that women are relational and men are transactional.

In reality, the most effective men and women switch throughout the day between relational behaviors and transactional behaviors depending on context. A cross-functional meeting before a high-stakes deadline demands a more transactional leader. A team meeting following a layoff requires a relational approach.

How to handle transactional and relational people

Navigating transactional and relational people is about leading productive conversations. This requires a thoughtful approach before, during and after the conversation.

Before the conversation

• Know thyself - Reflect on what mindset are you in - more transactional or relational? Define some realistic goals for the conversation.

• Do your homework - What type of personal are you dealing with, more transactional or relational? If you do not know, who can you ask? What can you find online?

• Prep your questions - Your questions one of your most powerful tools for steering an effective conversation. Write them down beforehand.

During

Both relational and transactional people have one thing in common: they both want to be heard. But few people actually listen. That is your opportunity.

Three techniques to ensure you are actually listening AND make your partner feel heard:

• Summarizing - Restate what you heard from the other person and ask for confirmation that you have understood them correctly. This is as simple as “could I play back what I’ve heard from you to make sure I understand?”

• Mirroring - Repeat the last few words they say. If they share “Our highest priority this year increasing retention.” You simply respond “increasing retention” This kind of mimicry may sound crazy at first. But mirroring can be very effective. in a study, waiters who mirrored collected 68% more in tips.

• Listening with your body - Words are just one vehicle to demonstrate that you are listening. Great listeners use their whole body to listen, even when they do not agree with the other person. They make eye contact. They nod their head as they listen. They lean their forward into the conversation. They use their voice (pitch, volume, pausing).

After

• Follow-up - After an important conversation, send a note expressing your appreciation and show you were listening by summarizing your take-away(s). For this note, consider what medium will land best - email, text, instant message, or handwritten card.

By preparing beforehand, listening actively and following-up dilignetly you can achieve an effective conversation with any partner, transactional or relational. But a conversation is a means to an end, not an end in itself. Your impact ultimately lies in what actions you take based on the conversation.

Today’s interview is with Josh Fried, a friend of TfT and a seasoned deal-maker whose experience spans commerce, mobility and crypto. I routinely learn new things from Josh and I think you will too.

I’m excited about the gems of wisdom these conversations can bring to TfT readers but I will need your help. If there is someone you’d like to see featured in an upcoming edition of Behind the Handshake, let me know who and why.

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Hi Josh, tell us about yourself.

I'm a native Southern Californian who has lived most of my life in Northern California. I’m 50% Italian and 100% Jewish, which means I feel guilty 150% of the time. I’m an adult fan of Legos. I have more shoes than my wife. I’m famous for an authentic Chewbacca yell. I love watching sports, and I’ve somehow raised two teen girls in San Francisco to be proud Dodgers fans.

If you and I were sitting next to each other on a flight, how would you describe your company and your role?

I'm a business person who works in crypto and blockchain technology. I work for the Solana Foundation, which supports the Solana blockchain. My job is to grow the impact and prevalence of this blockchain technology stack among real-world users, such as merchants running online or brick-and-mortar storefronts, or sports teams figuring out the intersection of loyalty and ticketing. I'm trying to use blockchain tech to improve the real world. Fundamentally, my job role could be called BD, Partnerships or Growth.

What is an unpopular or contrarian view you hold?

I continue to view blockchain technology as really valuable, with use cases like ownership of digital goods, or programmatic smart contracts that can enforce laws. For example, I worked with a startup that embeds blockchain addresses into invisible molecules that helps to prove the authenticity of collectible, luxury liquor bottles. Working with Solana Labs’ loyalty platform, Bond, allowed this startup to offer real transparency and trust in the rare spirits market - a solution than can apply to a wide variety of industries and use cases.

Tell me about a partnership that you're proud of and a lesson you carry with you today from that deal.

A big deal I’m proud of from early on at Solana was with ASICS, the shoe company. Together we sold a custom, Solana-inspired line of ASICS shoes using stablecoins, which are crypto digital dollars. ASICS is a global, 75-year-old company in a traditional business (apparel) that was willing to take a leap with us to show what's possible with blockchain and crypto. It made a big splash when Solana wasn't a household name, and we became known for that innovation.

My business partner at ASICS filled out our general "contact us" form, which nobody was really monitoring. So, the lesson is that you have to be open to looking for leads everywhere. Great partnerships can come from unexpected places, including the public-facing website lead gen form.

What is one insight that is core to how you approach relationships and build partnerships?

We're not doing deals with AI agents yet - every partnership takes place between people. So you actually have to get to know these people as human beings. While you can be transactional in partnerships, I don't think that serves you well long-term. Bringing it back to the ASICS example (above), I'm still in touch with my contact there. I know about his family and life outside of work. We invite each other to events when we are in the same area; it's become a true friendship. This has led us to brainstorm new partnership ideas every few months, even though our biggest collaboration happened years ago, because we nurture that human relationship.

What is one thing you have found to be true about negotiations but is often overlooked?

Even though I know negotiations aren't really zero-sum games, I sometimes get caught up in the winning aspect. But if I remove the emotional component of “winning,” I find I drive toward better outcomes. That is why I do my best written negotiation work when I compose a response and come back to it later. This removes the emotions.

What advice would you offer to someone earlier in their career that you wish someone had given you?

Early in your career, focus on surrounding yourself with good people and try to work directly for great people. This will pay off for the rest of your career; you'll reap the dividends from those early relationships. This is much more important than your role, your title, or how much money you're making in your 20s. I once heard someone say that your 20s are for networking, your 30s are for learning, and your 40s are for earning. There is a lot of truth in that.

What is something you read or listen to that makes you smarter?

Tangle - there are very few news sources nowadays where you get a truly unbiased perspective and this newsletter does its best to unravel one topic a day from the left and the right. And then the author adds his perspective. I find it fascinating.

Ezra Klein's podcast makes me smarter.

What is a book that has changed your perspective?

The Anthropocene Reviewed by John Green - this book does a great job of taking the long view, showing that we're specks of dust in the universe and we need to do our part to maintain this fragile and fleeting world.

This Is How It Always Is. It's a novel, loosely based on a true story, about a family discovering their child is trans. This book puts you in the perspective of the family, watching, understanding, and realizing their child is in the wrong body. Until you read something like that, it is hard to grasp.

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Today I’m highlighting Trump’s tariffs because trade impacts each of us and trade alliances are some of the most consequential partnerships of all. I see lessons here that apply to anyone forging partnerships.

But TfT is not turning into political punditry.

As the value of my stock portfolio sunk lower and lower in the wake of Trump’s tariffs, I did what I typically do in the face of global panic. I scrolled for some glimmer of hope.

What I found instead was an alternative scenario for how events could have unfolded differently. In his NYTimes column, Tom Friedman wrote this:

“When you have a country as big as China … the only way to negotiate is with leverage on our side of the table. And the best way to get leverage would have been for Trump to enlist our allies in the European Union, Japan, South Korea, Singapore, Brazil, Vietnam, Canada, Mexico, India, Australia and Indonesia into a united front. Make it a negotiation of the whole world versus China.

Then you say to Beijing: All of us will gradually raise our tariffs on your exports over the next two years to pressure you to shift from your export economy to a more domestic-oriented one. But we will also invite you to build factories and supply chains in our countries — 50-50 joint ventures — to transfer your expertise back to us the way you compelled us to do for you. We don’t want a bifurcated world. It will be less prosperous for all and less stable.

This approach harnesses the alliances the United States has cultivated for decades. It also invites China to participate in a solution aimed at achieving shared objectives. This line in particular stands out:

“We don’t want a bifurcated world. It will be less prosperous for all and less stable.”

The leaders of China and the United States differ on many issues but one thing is certain - they both want prosperity and stability.

Friedman’s view is similar to Peter Orszag, the CEO of Lazard, one of the world’s preeminent financial services firms. He recently shared this:

If your goal is to de-risk or isolate China, what you want to do is have North America and Europe together and reach some common purpose on what you’re trying to do. Because the throw weight of that combined entity is so large that it will affect everything else that happens in the global economy.

Professor Rush Doshi, an expert on China at Georgetown University’s School of Foreign Service, recently proposed a new, alliance trade strategy in an essay “Underestimating China.” He writes:

“China possesses scale, and the United States does not - at least not by itself. Because its only viable path lies in coalition with others, Washington would be particularly unwise to go it alone in a complex global competition.”

Whether or not you agree with Friedman, Orszag and Doshi, the strategy they advocate for is clear - alliances are the best way to gain leverage against China.

This highlights a fundamental problem with Trump’s tariffs.

What is the strategy?

It is clear that Trump likes tariffs. But what is his strategy?

Why a 25% tariff on Canada? Why a 50% tariff on Lesotho, a country whose economy is smaller than that of Duluth, Iowa?

What problem is Trump trying to solve?

• Generate revenue?

• Bolster national security?

• Reshore U.S. manufacturing?

• Gain leverage in order to lower tariffs?

Some of these objectives are in direct conflict with each other.

Even some of Trump’s conservative supporters, like economist Oren Cass, have called for more clear messaging, “The American people, markets, and allies all need to understand what is happening and why if they are to support or at least accept the administration’s plan.”

Maybe Trump is keeping the answer to these questions close to the vest as a negotiating tactic. Or maybe he is just figuring out a plan in real-time.

Strategy before partnerships

Whether negotiating with another country or another company, the first question is the same: what is our objective?

In technology, partnerships tend to help to achieve a few of objectives - (1) acquire new customers, (2) retain customers longer, (3) enhance the product or (4) drive awareness.

For example, Shopify’s objective is to make it simple for businesses to sell online. To achieve this, Shopify needs a seamless solution for online payments. That is why Shopify relies on a partner - Stripe. Shopify’s partnership with Stripe enhances Shopify’s product and retains customers longer.

This Shopify / Stripe example makes strategy sound easy. In reality, strategy is arduous. Before partnering with Stripe, Shopify had to decide whether to build their own payment solution. Or buy an existing payment solution. Or partner with another payment provider, like Paypal or Adyen.

To be successful, partnership leaders must be immersed in corporate and product strategy. If your company or product lacks a clear strategy, you need to help craft it. If your partner does not tie directly into your one of your company or product’s top strategic priorities, you should focus on other partners.

Partnerships may be your remit and your job title but strategy is central to your success.

Strategy before partnerships.

For more info

• Cited above

  • Tom Friedman: What Trump Just Cost America

  • Rush Doshi: Underestimating China

  • Peter Orzag interview

• Trump’s tariffs

  • Debate - Economists panel

  • Support - Oren Cass: Happy Liberation Day to Those Who Celebrate

  • Criticism - Noahopinion: All the arguments for Trump's tariffs are wrong and bad

  • Comedic criticism - John Oliver, Last Week Tonight

  • Predictions - Henry Blodget: Playing out Trump's game of tariff chicken...

The founder of one of those companies called me recently for advice on hiring their first partnerships leader.

Here are some key issues I suggested they consider before selecting the best candidate:

1. Compensation structure: Landing initial, high-impact partners and a repeatable revenue model will take time. Given this, I recommend a compensation model that rewards a strategic approach rather than transactional velocity. Quality over quantity. Annual not quarterly bonus.

2. Interview panel: Your first partnerships lead must have strong relationships with your other functional leads (e.g. Sales, Legal, Finance, Marketing). Their support on this hire is key to the candidate’s success in the role. They should be the interview panel.

3. Quality of their questions: The best candidates will shine with the questions they ask. Do they use the interviews to probe in ways that reveal they understand the challenges they will face in this role? Do they ask questions that show they are thinking ahead to the next stage of your partner program?

4. Partner types: Ask your candidates to stack rank their experience among the most common B2B partner types: (a) services, (b) tech/ISVs, (c) resellers, (d) cloud. Compare their answers to your company’s needs.

5. Deal types: Early on, it is more likely that you need someone who can land and scale a few strategic partners (whale hunter) rather than onboard dozens or hundreds of partners (net fishing). Make sure to dig into the types of partners and deals they have landed.

6. Company experience Dig beneath the resume. Some partnership leaders from BigTech bring complex deals experience with early stage products. Some startup partnership leaders lack experience with complex, cross-functional deals.

7. Title and hiring terms: Do not reflexively hire a VP of Partnerships. Instead, reflect on what title makes the most sense given your company's stage and situation. Also, are you sure you are ready for a full-time hire? Would a 6-month contract or a fractional partnership lead be a better fit right now?der.

While the advice was crafted for a startup founder, it is just as valuable if you are looking for a role leading partnerships.

Build your narrative around the challenges you’ve faced and how you overcame them.

Anticipate questions about the partnerships you’ve led, the deal types you know and the companies where you’ve worked.

Prepare as much for the tough questions you will ask as the answers you deliver.

Good luck!

And don’t hesitate to reach out if I can help you find your next role.

That line captures a sad reality: New Year's Day is the wet blanket of the holiday season. New Year’s Day has no well-defined food or traditions. It is a day more known for recovery than celebration.

I view New Year's Day as a chance to reflect and prepare.

That is why I made it a tradition here at This for That to greet readers on the first morning of the New Year with an uplifting message to start the year:

• 2021: Better than New Year's Resolutions

• 2022: How will you fail this year?

• 2023: This year, find you inner Karikó

This year, I’m offering you a quote from one of my favorite writers. I hope it spurs you in 2025.

You'll also find a collection of my favorites from 2024 below.

Craft your own narrative

Michael Lewis, the bestselling author of non-fiction books like Moneyball and The Big Short, has spent years interviewing people and turning them into characters in his books. He listens carefully to the narrative they craft about themselves to inform the the character they become in his book. In doing so, Lewis understands how the stories we tell ourselves come to define us.

Michael Lewis said this during an interview in 2020:

“As I got older, I could not help but notice the effect on people of the stories they told about themselves. If you listen to people, if you just sit and listen, you’ll find that there are patterns in the way that they talk about themselves. There’s the kind of person who’s always the victim in any story they tell – always on the receiving end of some injustice. There’s the person who’s always kind of the hero in any story they tell. The smart person – they deliver the clever putdown. There are lots of versions of this. And you’ve got to be very careful about how you tell these stories because it starts to become you. You are, in the way you craft your narrative, kind of crafting your character. And so, I did at some point decide I am going to adopt, self-consciously as my narrative, that I’m the happiest person anybody knows. And it is amazing how happy-inducing it is.”

There is so much I will not be able to control this year, like the economy, my health and the behavior of those around me.

But, as Michael Lewis points out, I can craft the story I tell myself about who I am. I can define my own character.

You can too.

Top TfT Posts 2024

Based on pageviews, the top This for That posts this year:

• How I got past getting laid off

• Truth to power

• The Story of the Global Data Alliance that is Mapping our World

My Favorites from 2024

• TV shows:

  • Industry (Max)

  • Black Doves (Netflix)

• Movies:

  • Drama: Whiplash (Amazon), 2014

  • Comedy: Hit Man (Netflix)

  • Animated: Inside Out 2 (Disney+)

• Books:

  • Fiction:

    • James, Percival Everett

    • Bel Canto, Ann Patchett (2001)

  • Non-fiction:

    • King: A Life, Jonathan Eig

    • The Showman, Simon Shuster

• Songs:

  • Hip-hop: They Not Like Us, Kendrick Lamar

  • Country: Bar Song, Shaboozey

  • Pop: Two Days into College, Aimee Carty

• Podcasts: too many to list but here are a few standouts:

  • Justice: This American Life - This is the Case of Henry Dee

  • Technology: NYTimes Daily - Real Teenagers, Fake Nudes

  • Business: Invest Like the Best - Matt Perelman & Alex Sloane

• Newsletters:

  • Economics & policy: Noahpinion

  • Technology: Lenny’s Newsletter

  • Fun: 5 Tweet Tuesday

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If you have any suggestions for TfT posts in 2025, including partnerships you want to see covered or partnerships challenges, please reply and let me know.

Oceans shape our lives in ways we overlook - commerce, climate, food supply, tourism, national security, etc. And there is a shocking amount we still do not yet know about the ocean. For example, what shapes ocean currents?

Until recently, understanding the ocean relied largely on expensive research ships with highly-trained crews.

Then, in 2012, Saildrone emerged.

Saildrone may be the coolest company you don’t yet know.

And when you learn how Saildrone began, you may find the story as inspiring as I do.

It started with a passion project

Richard Jenkins grew-up in a small town on the coast of England where he learned to sail similar to the way many kids learn to ride a bicycle. As a freshman at Imperial College, Richard learned that a team that had just broken the world record for land-wind speed. They had built what is called a “land yacht” - a wheeled vehicle with sails - that traveled 116 mph by harnessing the wind.

Richard became obsessed with breaking that record.

He formulated a new rigid sail design. He became an expert in lightweight materials, like carbon fiber. He lived in the desert to study the wind.

Richard dedicated 10 years of his life to breaking the land-wind speed record.

To cover his costs, he did odd jobs. He slept in his car. He estimated that he lived on $1,000 a month for years.

In 2009, on a dry lake bed in the Mojave desert, the vehicle Richard had designed reached 128 mph.

Richard Jenkins had broken the land-wind speed record.

From land to sea

After achieving the goal he had chased for so many years, Richard confronted the question that successful Olympic athletes and startup founders also face: what next?

He had a world record but little money and no clear direction. He was unmoored.

To pay his bills he built kiteboards. On the side, Richard continued to tinker. He wondered if he could apply what he had learned about aeronautics on land to the high seas. He enlisted some friends and together they removed the wheels from his record-breaking vehicle to test its viability in the water.

They decided to try to sail their prototype from San Francisco to Hawaii with no crew onboard. Instead, they used remote controls to capture wind and solar energy.

In 2013, their autonomous sailboat reached the shores of Hawaii in 34 days.

Jenkins had collected another world record. But did he have a product that anyone would pay for?

An initial partner

Next, Jenkins and his small team brought their prototype to a meeting with the National Oceanic Atmospheric Administration (NOAA), responsible for national weather forecasting and storm warnings. Richard proposed that NOAA could use the prototype to collect ocean data more cost-effectively than NOAA’s standard crewed research vessels.

The NOAA team was very interested. But the problem was trust.

NOAA is a federal agency with a $7B budget entrusted to them by taxpayers with oversight from Congress. NOAA avoids projects with risky, early stage startups and their untested founders and unproven prototypes.

The team at NOAA proposed a special agreement, called a Cooperative Research and Development Agreement (CRADA). These agreements allow collaborative research and development between federal agencies and private companies. There is no financial commitment from the US government but the startup gets access to government facilities and a defined problem to solve that can help attract investors.

The initial project with NOAA produced a joint research paper. That led to another project. And then another.

From a pilot partnership to a purpose

Since 2014, Saildrone has transitioned from a drone hardware company into a data company. “People look at Saildrone and think we’re a hardware company, but the hardware is just twenty percent of the puzzle,” Jenkins says.

Saildrone licenses ocean datasets that covers the cost of building and maintaining their fleet of “uncrewed surface vehicles” or “USVs.” (I prefer to call them “fancy autonomous sailboats”)

Saildrone helps to saves taxpayers money.

A typical maritime research vessel costs $35,000 a day to operate, or about $12M annually, and carries a crew of 30. A Saildrone USV, on the other hand, operates for $3,500 annually without any crew … no need to stop at a port every few weeks.

Saildrone has expanded its partnerships. Today, Saildrone helps the US Department of Homeland Security (DHS) track illegal fishing, drug smuggling and human trafficking. They help the US Department of Defense (DOD) survey the ocean for submarines. Their ocean data is used by telecommunications and energy firms that operate businesses on the ocean floor.

Saildrones have faced 126 mph winds while collecting storm data at the center of a Hurricane Sam (2019). They completed the first unmanned circumnavigation of Antartica (2021). Two Saildrones were even temporarily captured in the Red Sea by the Iranian Navy (2022).

Saildrone is now valued at over $1B.

The lesson from Saildrone

Richard Jenkins and the story of his founding Saildrone may sound distant and disconnected to your own journey.

But I see something universal in Richard’s story.

Each of us is searching for the center of a venn diagram that unites our skills, our interests and an income. Finding that elusive combination requires a relentless drive, even in the face of numerous setbacks.

I have no doubt that Richard had friends who made snide remarks when he told them, “yes, I’m still chasing that world record.”

But he marched forward. He broke that record.

Afterwards, I imagine they chuckled when he told them “I’m not sure what’s next for me. I’m trying to figure that out.”

But he marched forward. Eventually, he started a company to pursue his interests and his skills.

Later, I’m sure they snickered when he mentioned “I might have landed a pilot partnership with the federal government.”

But Richard marched forward.

You should too.

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Sources

• https://www.saildrone.com/news/how-saildrone-wing-was-born

• https://www.bloomberg.com/news/features/2018-05-15/this-man-is-building-an-armada-of-saildrones-to-conquer-the-ocean

• https://www.fisheries.noaa.gov/science-blog/what-saildrone-and-what-does-it-do-nwfsc

• https://research.noaa.gov/historic-noaa-saildrone-mission-did-more-than-set-records-its-helping-scientists-improve-hurricane-forecasts/#:~:text=PMEL%20began%20a%20partnership%20with,%2C%20software%2C%20electronics%20and%20operations

• https://news.usni.org/2022/09/02/iran-temporarily-captures-two-u-s-saildrones-in-red-sea

The recommendations below are a few small things that I am thankful for this year and I thought you might also enjoy.

I have so much to be thankful for this year, including you. Thank you to the entire This for That community.

Laugh - I am embarrassed to admit that an instagrammer I discovered recently called Mom’s Dad Jokes makes me smile every week. Checkout her jokes and her delivery and you’ll see why.  If you’re prepared to face some eye rolls, consider sharing some of her jokes at your next family dinner: 

• Want to hear a potassium joke? K. 

• What do you call a computer that can sing? A Dell. 

• I got a lot of jokes about retired people. But none of them work. 

Low-cost luxury - I recently Marie Kondo’ed my sock drawer. I pulled out each and every sock and only invited those back into the drawer that I truly enjoy wearing. The others I tossed. That is when I realized something: I needed new socks. I conducted some research (“sock-search?”) and discovered Thorlo socks. They make my feet happy. And when my feet are happy, I am happy. 

Lunch - I work from home a few days a week and for lunch I want something that tastes delicious but does not take long to prepare. This tuna mayo rice bowl is a meal I can have ready in 4 minutes. It is simple, delicious and healthy. Props to NYTimes Cooking (paywall). 

• Tuna: 1 can

• Rice: I suggest 90 second Uncle Ben’s Coconut Rice (3/4 of a bag)

• Mayo: 1 - 2 tablespoons

• Sesame oil: 1/2 teaspoon

• Soy sauce: 1 teaspoon

• Sesame seeds - sprinkle on top

• Optional: avocado, sriracha

Learn - There was an era of the internet when everything was free and easy to access. Sadly, those days are gone. Now, we live in a world of paywalls and registrations. I fear we are in the final stages of that free era of podcasts. But for now, here are a couple of my favorite podcast episodes from the last year. Enjoy them free of charge while you still can:

• Invest Like the Best: Sean Feeney interview (March 26, 2024) - this is a conversation about art, commerce and service with a Wall Street trader who quit his job to help his friend, a world class chef, start her own restaurant. Sean has so much passion about re-thinking the restaurant business.

• Today Explained: Why ‘Country Road’ Feels Like Home (July 3, 2024) - this episode explains the global popularity of a 50-year old song about a US state with a population smaller than Houston.  

Love & Kindness - Loving yourself and others often involves facing difficult questions. There is no textbook with answers. But Cheryl Strayed’s book Tiny Beautiful Things may be the closest thing that I have found. Her collection of her “Dear Sugar” newspaper columns showcases a compassion we all could benefit from as we each navigate love, friendship and family. It is a book filled with tiny beautiful ideas. I recommend the audiobook read by the author.

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