Embrace Collaboration: Interview with Jason Finger, Co-Founder and CEO of Seamless

I recently went one on one with Jason Finger. Jason was the co-founder and longtime CEO of Seamless,  which merged with GrubHub in 2013. Jason is the Chairman of Upper90, a leading provider of revenue and collateral-based lending solutions to emerging businesses, and Chairman of The Finger Group, a business accelerator and stage-agnostic private equity firm. The Finger Group has helped to launch and grow, as an engaged investor and/or operator, companies including Thrasio, LiveAuctioneers, Procore Technologies, ZocDoc, BlueApron, Clio Themis Solutions, Klout/Lithium, InvisionApp, Conductor, Clearbanc, Betterment, Freshly, YipitData, Crusoe Energy Holdings, Octane Lending, Clutch, SeatGeek, GoSite, Skillshare, Slice, SinglePlatform and Stone Ridge Holdings.

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks or challenges have been most instrumental to your growth?

Jason: My entrepreneurial spirit was sparked by my mother and aunt, who operated a very small jewelry business when I was growing up.  While their business had challenges, it motivated me to want to start my own business.  I wanted to create jobs for others that were secure, in a manner that improved people’s quality of life -- and to help the small and medium-sized businesses.  That direction led me to co-found Seamless and then invest in a number of other brands that engage, inspire or assist people.

I also developed a passion for helping founders and executive teams to minimize dilution with their financing decisions so they could maximize the fruits of their labor should their business achieve success.  That led to the launch of Upper90, a fund dedicated to utilizing both credit and equity in creative ways so that early investors and teams can maintain maximum ownership in the businesses they’ve developed.  While I certainly enjoy investing and lending, the best part for me is to learn about new business models and new challenges and to try to help the operating teams.  Companies are made up of people.  It’s those personal connections that have the most meaning for me.

Adam: How did you come up with your business idea? What advice do you have for others on how to come up with great ideas?

Jason: The idea for Seamless started when I was working at a law firm, working late many nights, and needed to order dinner in.  I was the one who collected everyone's order and put on my credit card for the points. I realized that web-enabled menus would make everyone's life easier which ultimately led to the creation of automating restaurant takeout. But, like most businesses, the idea we started with wasn’t the idea we ultimately launched.  My co-founder and his brother and I all iterated on the initial concept.

Great ideas are generally just concepts that solve definable problems.  Problems exist all around us.  I think the mindset of looking at problems as opportunities and then, most importantly, executing on those opportunities is key.  Many people have great ideas.  But, they stay great ideas in someone’s mind.  In sports and in life, you miss 100% of the shots you don’t take…

Adam: What are the key steps you have taken to grow your business? What advice do you have for others on how to take their businesses to the next level?

Jason: At Upper90, we are focused on creative ways to fund businesses and help them grow. While most founders think traditional venture capital is the only way to fund their business, my advice would be to research creative ways that may help their bottom line in the long run. We often say ‘delay your (Series) A’ so that founders can rethink how they raise money.

Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?

Jason: To me, leadership starts and ends with connecting action to a higher purpose. Your mission and values should drive everything you do, in terms of business goals as well as being aligned with the people you work with.

Adam: What is your best advice on building, leading and managing teams?

Jason: I look at hiring a team with the same lens as the companies we invest in. I like to work with strategically thoughtful people with a growth mindset, who want to work on interesting and significant challenges that can have broad impact, and who possess relentless grit. This combination of attributes brings a level of excitement and constant learning that makes working together fun and interesting every day. Outside of that, find people who have a skill or a perspective that you admire — or even that you want to avoid. And then build a relationship with those people in a manner that helps you and helps the business grow.

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders?

Jason: The first tip is to follow your passions.  Pursue an idea because you love it, not because it’s the next big thing.  Whatever direction you follow, it will be the focal point of your life, so make sure it’s something you enjoy doing.

Second, make sure to listen to others.  In fact, listen more than you speak.  Remind yourself that complaints and constructive criticism are often more valuable than praise. When you stay open to others’ opinions and feedback, you can view your product or business model more objectively to be able to deliver what your customers or investors are looking to gain.

Third, embrace collaboration.  That’s where true leadership lies. Ask your team for input and ideas, regardless of their job title. In my experience, collaboration breeds innovation, which is critical to any business.

Adam: What is the single best piece of advice you have ever received?

Jason: My most valuable lesson I actually learned from a quote.  There is a saying that success has many fathers but failure is an orphan.  When I first heard that, I was starting Seamless and I interpreted it to mean that when there is a successful outcome, many people take the credit.  And, when there is a failure, no one wants to take responsibility.  It actually put a lot of pressure on me and I remember thinking to myself, better not screw this up as that will be all on you--I was going to single-handedly will the company to be the market leader.  I felt like I needed to do everything and be involved in every decision.  But, as we executed and I started learning more about management and talent development, I began to see an alternate interpretation, especially as I had become the bottleneck on many decisions.  Perhaps the proverbial fathers and the orphan were the inputs.  Maybe, if I built a team of “mothers and fathers” versus continuing on the path of feeling like I needed to “go it alone”, I would enhance our probability of “success”.  This completely reframed my thinking. I began to recognize that the people on my team were an asset, not an expense.  It is not that failure is an orphan--it is that by yourself the probability of failure is massively higher than it would be with a team that executes at the highest levels. 


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal winning athletes, political and military leaders - for intimate half-hour conversations each week. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities and non-profit organizations.

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