Ten years ago, on December 18, 2008, I dropped out of Harvard Business School -- in the heart of the worst recession in 81 years -- to start my company. There I was, sole founder, by myself, with nothing but a dream.
Unfortunately for me, New York City was not yet a robust community of startups and entrepreneurs. There was one angel fund, two or three venture funds that didn't take meetings with early-stage companies, no tech incubators, no Y Combinators, no General Assembly. To say I was daunted was an understatement. So, I opened up my laptop, and simply got to work.
First, what I realized is that starting a company was pretty much like climbing Kilimanjaro, which I've never done by the way. And if I was going to make the climb, how would I hack it? I set out to find people who had done it and ask them: How did you train, what did you pack, what season did you go in, and who did you take with you who knew the safest routes?
I met an incredible couple named Tiffany and Jon Cowley and they helped me envision and map out the website. Jon joined as head of product design and Tiffany was creative director. Then, I started engaging anyone and everyone who I thought would love the mission of LearnVest, which was to provide accessible and affordable financial planning for all Americans.
Over a span of two years, I found some amazing formal advisors who believed in what I wanted to build, but who had different focuses and different backgrounds. Greg Coleman, president of Buzzfeed; Susan Lyne, former CEO of Martha Stewart Living Omnimedia, then CEO of Gilt Groupe, now head of AOL's BBG Ventures and Ann Kaplan, one of the first female partners of Goldman Sachs, among others.
After getting a critical mass of advisors in those first 24 months, I onboarded new mentors twice a year. There's a metric that says you should be collecting at least one new smart, savvy person to help your business per year. If you're hustling and talking to the best and the brightest, you need to be talking to two to three people a year, one of whom will ideally become enrolled in your vision in some way.
It's important to note that I grew up in Jacksonville, Florida. I did not have a special lifeline to important people like Ann Kaplan or Susan Lyne. A college student I knew put me in touch with Ann Kaplan and I met Susan Lyne through an intro. I opened my Rolodex, scoured LinkedIn and Facebook, and connected and requested meetings with anyone who was experienced and knew more than me, which at that point was literally everyone.
There were three key things that got them excited about advising and investing us.
- They believed in the purpose: helping give American families better access to their wallets.
- They realized I was crazy enough not to give up.
- I made it worth their while: everybody got some form of equity in the business.
But gathering advisors is a dynamic process. So I kept at it. To every person I met, I would ask: Was there anybody in your network who I should be talking to about this idea? It was simple, but it was the most important question that I asked because out of it came tons of people who believed in our mission and helped us build the business that ultimately sold to Northwestern Mutual.
I recommend that all entrepreneurs have a board of advisors who rotate out (a three-year vesting contract is an industry standard) as you need different skill sets -- whether it's fundraising, technology, regulatory and compliance experience, marketing, or media; get the best person in each of those spaces.
And listen -- there were a lot of "no's." But no's are okay. I never took no for an answer. I took it as "not now." I would look at people and say, "no hard feelings; you're super busy. I'd love to come back to you in a year and see if that changes."
At least once or twice, someone who initially passed on my company came back at a later date to advise or invest. In every case, they were impressed by my commitment and resilience and that I hadn't given up.
It's so important to know that fancy connections and impressive degrees aren't the only way to get a meeting. We all have networks. Leverage yours in all ways. Ask the most successful people you know for connections - "is there anyone else you think would be a really good mentor for me?" Keep it simple and ask the right questions. Go to conferences that matter in your industry, whether that's retail or fintech. Seek out the smartest person you heard speak. Pick up their books. Reach out to them. More often than not, people who are innovators care about helping other people innovate. It's a community of people who want to see others succeed.