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Quick note: I’m kicking around an idea related to this issue that I mention at the end. I'm still deciding, but would love to hear what you think.
There's an old quote, credited to Abraham Lincoln, that if he had six hours to chop down a tree, he'd spend the first four sharpening his axe.
I love that quote. I've repeated it probably a hundred times to colleagues over the course of my career. Because I believe that the people who win in their careers are the folks who prepare the longest, work on their skills, and show up doing the best possible version of their work.
But for entrepreneurship, I think it's the wrong advice.
I know a guy I'll call Ben. Ben ran sales at a healthcare tech company in San Francisco focused on pricing transparency. He went to an Ivy League school, and you could tell when you met him. He was super smart, sharply dressed, and well-spoken. But more importantly, he was a brilliant operator. The kind of guy who could build out complex go-to-market plans that left CEOs feeling confident.
We came up in the same industry and knew most of the same people. But I was what you might consider a "poor man's version" of Ben. He was running revenue at a company well north of $250 million, managing sophisticated partnerships and a complex sales process. I was at $70 million, without most of the complexity. We were both good at our jobs, but if you'd lined us up in 2018 and asked anyone to bet on who would be a successful entrepreneur, nobody would have picked me.
Like we all assumed he would, Ben eventually went out on his own to build a healthcare technology consulting firm. And when things didn't take off the way he expected, he followed the old Lincoln adage and sharpened his axe. He built more frameworks, better processes, and deeper methodologies that would resonate with clients. He believed that excellence alone would lead to success.
But it turns out that working on getting better didn't actually work.
And the last time I spoke with him, his business still hadn't found its footing. He was trying to make fractional work stick and applying for VP jobs back in the Bay Area. It's hard to understand why Ben couldn't translate his smarts, expertise, and excellence into successful entrepreneurship. Because by every measure of merit, he deserved to win.
In 2019, I launched my own healthcare consulting business. I didn't have the patience Ben had, and I didn't have the runway to find out if being the best consultant I could be would eventually pay off. The pressure to make my business work fast was real. Going back to a regular job wasn't something I wanted to do.
So I took the opposite approach.
Rather than trying to become the best consultant I could be, I decided that I was going to start putting myself out there in every way I could think of. I wrote on LinkedIn every single day. Posts about healthcare and sales and building teams, hiring, firing, go-to-market, and everything else I'd spent sixteen years learning. I hit the podcast circuit like an absolute madman. Hundreds of them. Any show that would have me. Any audience that might include a single person who needed what I had.
Every morning, I scoured Google News and found all of the healthcare founders who had just announced a funding round, and sent them a DM. Congrats on the round. I'm a healthcare technology veteran from Zocdoc and PatientPop, and I love what you're building. Let me know if I can be helpful. I sent thousands of those DMs over the course of two years. Some founders ignored me. Some responded. And some became the first clients in my new business.
Then I did it all over again. DM. DM. DM. More posts. More comments. More podcasts. Networking event. Connecting two people. Cold email a VC firm. I was reaching out to anyone who I thought might need what I was offering or could point me in the direction of someone else who did.
I didn't even have a strategy. I was just swinging my axe.
After a while, a few discovery calls started trickling in. Some of them came from writing valuable LinkedIn posts. A few from DMs that landed at just the right time. One or two from podcast appearances. Then, one of those appearances found its way to Jason Lemkin of SaaStr. Turns out he had also seen some of my posts on LinkedIn, and he invited me to speak on stage at SaaStr Annual in San Francisco. After my presentation, several founders lined up asking if I offered consulting. The recording of my talk hit YouTube, and even more calls started to come in. And then in April 2020, after posting on LinkedIn daily for seven months, one of my posts finally exploded. It generated millions of impressions, tens of thousands of engagements, and five thousand reshares.
Thirty people booked calls that week.
If you looked at any of those things in isolation, it's easy to pass them off as luck. Jason Lemkin hearing me on some podcast. The YouTube video being seen by founders who just happened to need some help. A post going wild and hitting millions of impressions out of nowhere. I understand why each one looks lucky. But the truth is, you don't get a one-in-a-thousand break without taking a thousand swings first. I'd been putting myself out there every single day, and eventually the math had to work out in my favor. The break that looks lucky from the outside is just compounded volume finally paying off.
The craziest part is that I hadn't actually gotten any better at consulting during my entire push for more exposure. My skills were basically the same. My expertise was hardly different than it had been the very first day I opened my business. What changed was that I had become almost impossible to miss.
Ben had an exposure problem, not a preparation, excellence, or expertise problem. The market doesn't reward the most talented people. It rewards talented people who are also visible. Once you're past an above-average threshold of competence, "getting better" barely moves the needle. What moves the needle is getting your face and your brand and your thoughts and your expertise in front of as many relevant people as humanly possible.
We don't hear this growing up. We hear about working harder and getting better. That the best person wins out in the end, and the quality of your work will be what sets you apart. I just don't think that's true when you're getting started as an entrepreneur.
So if you've been trying to work your way out of a failing business by "improving your skills," I grant you permission to stop. Because the number of people who know you exist is what matters right now.
You're talented just like Ben or me. Your axe doesn't need any more sharpening.
It needs you to start swinging.
That's all for this week.
See you next Saturday.
P.S. Exposure still seems to be the biggest issue for most entrepreneurs. I recently gave a 90-minute talk at a private mastermind to more than 50 six- and seven-figure creators on how I'm still growing on social in the age of A.I. (while most accounts are stagnating or declining). My process, systems, what’s working, what isn’t, etc.
I'm considering turning it into a polished version that I can do live for readers, but it would depend on how many people are actually interested. It would be a paid ticket to cover my time but, as always, at a highly accessible price point. If you think it would be beneficial to you, you can learn more and let me know if you’re interested here.
