Why was I so blinded by his money?
Like most young entrepreneurs, early in my career I was eager for mentorship. I excitedly tracked down as many nearby people as I could with the word “entrepreneur” in their LinkedIn bios and found ways to meet them for coffee.
Thanks to those meetings, I learned a ton, and I’d certainly recommend a similar approach for any new founder. But be careful. Meeting with lots of experienced entrepreneurs means getting lots of different opinions and perspectives, and lots of the advice you get will be contradictory. One entrepreneur will tell you to do X, another entrepreneur — perhaps the very next one you talk to — will tell you to do Y, and, occasionally, those two things will be complete opposites of each other. After the conversations, you’ll be stuck having to decide which advice to follow.
This is exactly what happened to me. I’d scheduled two coffee meetings with experienced entrepreneurs in the same afternoon. The first meeting was with an entrepreneur who’d taken his company public and subsequently sold it for a few billion dollars.
I met him in the lobby of a swanky hotel, and I sipped a drink I only agreed to order because I knew I wasn’t paying for it. After all, I was a struggling, young entrepreneur, and cash was tight.
During the meeting, I demoed the app I’d built, he seemed to like it, and we spent most of the hour discussing what additional features would make it a surefire success. By the end of the meeting, he insisted I definitely needed to add one feature we both agreed would be “killer,” and, once I added it, I’d have customers lining up. Sure, the feature was a bit complex and would take a while to build. And, sure, it wasn’t exactly the direction I’d been going with the product, but the billionaire I was sipping lattes with in the lobby of a fancy hotel insisted people would love it, and that got me excited.
The second meeting was with an entrepreneur who wasn’t much older than me, had only recently raised a small amount of funding, and who seemed almost as interested in pitching me his startup as I was in pitching him. I honestly don’t even remember his name. I mostly just remember that we met at a dingy coffee shop in a not-so-nice part of town, and I was annoyed when I had to buy his overpriced latte. As for me, I stuck with water.
After he’d finished pitching me and trying to sell me on his startup, I demoed my app. When I was done, he hardly acknowledged what I’d built. Instead, he began peppering me with questions about my customer acquisition strategy. Who was my target customer? How much were they willing to pay? How was I going to reach them? And so on. I didn’t have many good answers.
By the end of our meeting, he insisted I needed to spend a lot more time learning my market and trying to figure out how to sell. A couple times I tried to ask him about features, and he brushed my questions aside. “Don’t worry about features right now,” he told me. “Your customers will tell you what features they want. You have to find them first.”
I ended the afternoon with a problem. I’d met with two entrepreneurs, and they’d each given me two completely different pieces of advice about how to proceed that would require all of my time., and I had to figure out which advice to follow. How was I going to decide?
Ultimately, I followed the advice of the billionaire.
Who wouldn’t? That was the guy who clearly knew more.
Fast forward a few months, I’d built the feature the billionaire insisted customers would line up for, and… well… you can probably guess what happened.
Nobody wanted to buy that new feature. Heck, I couldn’t even get the billionaire to return another email from me when I wanted to show him what I’d done. He ghosted me.
Within a few months, I shut down the company, throwing away all the time and effort I’d put into building that one killer feature the billionaire told me I absolutely needed, and I moved on to other projects.
Would following the advice of the other entrepreneur — the one who was clearly still struggling — have saved my company? I have no idea. But I do know that, in retrospect, it would have saved me time. I would have talked with potential customers, they would have told me they didn’t want the thing I was thinking of building, and I could have shut down the company sooner or pivoted to building something they did want. In either case, the outcome would have almost certainly been better.
I know that now, but I didn’t know that at the time. Part of the reason was because I trusted success instead of relevance.
In retrospect, the billionaire was giving me advice based on his perspective of running a big, successful, public company. But running a successful, public company is very different than launching a startup. During that latter phase of business building — the one most entrepreneurs aspire to but few reach — priorities surely change. He might have been giving great advice for founders trying to find ways of doubling their stock prices in two years, but it wasn’t necessarily good advice for someone at my stage of development.
In contrast, the other entrepreneur — the struggling one who wasn’t much farther along than me — had relevant, recent experience. He’d been in the same trenches as me not very long ago. Heck, we were surely still facing plenty of the same challenges. Because of that, he might not have had massive success, but he had valuable wisdom about what I need to do in order to clear the closest hurdle.
I couldn’t see that at the time because I was blinded by money and everything associated with it. Not that I’m alone. It’s an easy trap entrepreneurs can’t help but fall into because so much of startup success is defined by money — valuations, fundraising, exits, etc. All that talk of money blinds us to the importance of relevant knowledge.
When you’re deciding whose startup advice to follow, don’t focus on how much money the person has made. Focus, instead, on what that person has learned and, just as importantly, how recently the person learned it. Remember that, when evaluating someone’s advice, relevance to you and what you’re trying to accomplish is more valuable than a person’s accomplishments.
Author: Aaron Dinin, PhD