I Interviewed 25 Amazing Startups and This Is What I Learned


These days, we tend to think of the entrepreneur as a visionary, in the mould of Elon Musk, Jeff Bezos or Jack Dorsey – individuals with audacious goals who are determined to shake-up industries.

In doing so, we imagine these amazing individuals just sitting at a figurative “blank canvas”, dreaming of the next massive opportunity and then going for it. And, who knows, maybe a guy like Elon Musk does just that, but in my experience, interviewing twenty-five entrepreneurs (and counting) for the ‘Smart People Should Build Things’ podcast, I am yet to meet anyone of the “blank canvas” variety.

Just to be clear, I am not taking anything away from the very successful group of entrepreneurs with whom I have spoken. They have raised hundreds of millions of dollars in venture capital funding, employ thousands of people and are creating categories that did not exist only a few years back — entrepreneurs like Katia Beauchamp from Birchbox, Dane Atkinson from Squarespace and Sumall, Nick Taranto from Plated, Jon Stein from Betterment, Olga Vidisheva from Shoptiques and more.

However, in meeting all of these twenty-five entrepreneurs, I am yet to meet one who has told me that he/she has closed their eyes, started to dream something big and then went after it. In virtually all cases, the moment of inspiration has been fortuitous.

Now, what do I mean by “fortuitous?” I don’t mean that these entrepreneurs were lucky. I think that you are lucky when something happens to you, whereas these entrepreneurs were open to experience and ready to pounce when an opportunity presented itself. They had their antennas up at all times – possibly even unwittingly – knowing that businesses lurk in the problems we face in everyday life. I would categorize these entrepreneurs as the “There has got to be a better way” group.

Entrepreneurs Find A Way: Solving Problems Others Don’t See

One of my favorite guests was Laura Mather, who left ebay, where she was Director of Trust and Safety, to found her enterprise security firm, Silvertail Systems, which she ultimately sold to EMC for approximately $350 million. Laura described herself as a crime fighter at ebay, rooting out the bad guys, and she was frustrated by the reactive nature of her position. She told me that could not stand that it would take weeks to discover a massive fraud that had hit her customers – because ebay users would find the problems when they received their credit card statements.

So, she created Silvertail to identify strange click patterns and billing discrepancies, telling me, “We could detect these attacks at the moment they started and…notify people in less than an hour.”

Will Nathan encountered an entirely different problem, leading him to found Homepolish: he could not find an interior designer who would work with him on his apartment. “I was told to go to IKEA for my $30,000 budget…What other business do you show up at with that kind of money and they say, ‘go away’?” Will responded by leaving his positionat Buzzfeed to start this transparent platform through which you can hire an interior designer at a set hourly fee, rather than by marking-up purchases.

He seems to have discovered that “better way,” because he now employs three-hundred interior designers in eleven cities and has completed thousands of projects for clients who appreciate an hourly rate.

And, Laura and Will are not the only ones, of course. David Greenberg started Updater, a platform which helps you organize and complete all of your moving related tasks, after it took him five hours to update all of his addresses during a frustrating move. Apparently, venture capitalists agree that there has to be a better way because he has raised $15 million to develop Updater.

Customers certainly agree – Updater has helped hundreds of thousands of people move already. And, it goes on and on – many of our episodes are the stories of entrepreneurs identifying a “better way” and taking the leap.

Outliers and Insiders: Monitoring Opportunity

Of course, there are other types of entrepreneurs, who identify opportunities just as fortuitously. Another group, which I dub, “The Insiders,” works in and almost lives in an industry and are lurking as well — just waiting for the next big opportunity to present itself.

Serial entrepreneur, Dane Atkinson, who joined Squarespace as CEO as employee number three, left this juggernaut in 2011 and started Sumall, an “all in one social media and ecommerce platform,” which already serves 230,000 businesses. He told me that he was a “fan of data” but didn’t set out to start Sumall specifically, “We always pick paths that have matured over the decades that we have been in the game.”

Alexandra Wilkis Wilson, who co-founded the flash sales behemoth, Gilt Groupe, made the leap to join Glam Squad in its infancy, as its CEO, after she “fortuitously” ran into the founders and “fell in love, on the spot, with the idea.” She told me, “I downloaded the app, started becoming a client, every single day I had feedback for them, I later became an investor and the board of Glamsquad came to me and said ‘we want you to do this full time.”

Notably, she co-founded Gilt Groupe, while working as Retail Operations Manager at Bulgari, when the idea was brought to her by a friend. She was an insider and knew what worked – she saw her opportunity, because she was perfect for it, and jumped on it.

When I speak to aspiring entrepreneurs, I often hear, “I know I can do it. I just wish I had an idea.” In my experience listening to entrepreneurs, no one has truly been trying to think of the next big idea. Instead, this enormously successful cohort has maintained an awareness of the opportunities surrounding them and moved decisively when they saw their opening.

So, what does that mean for you? What can you do to advance your entrepreneurial journey?

  1. Walk through life with your eyes open, critically evaluating your experiences. (This one is easy!)
  2. When you encounter “pain points,” ask yourself if there might be a better way or if you have the inside knowledge to fix a problem.
  3. Truly consider whether this pain point exists for others, not just you.
  4. Determine whether fixing this problem can result in an actual business which you can execute on!
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