Behind the Handshake: Ross Siegel
The best freestyle rappers can spit rhymes that incorporate any word you give them: “archeologist” … “kumquat” … “virus.”
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.
