Why I mentor founders — and a special announcement!

I spend a lot of my “free” time mentoring startup founders.

I often get people asking me why, and I’m reminded of that scene near the end of The American President, where Michael Douglas takes to the lectern to finally defend himself against the cynical attacks of his opponent: “yes, I am… but the more important question is: why aren’t you, Bob?”

Not that I’m defensive or anything.

I imagine a disproportionately high share of my readership already agrees with me, but that shan’t stop me from preaching. ✊

So, here goes.

I spent the entirety of last weekend working at the Startup Challenge — not to mention a huge amount of time in August and September preparing for it. It was a weekend-long competition where 30+ startups came together to find as much traction in the marketplace as they could in just one weekend.

An event like this is mentorship at scale, and I’ve spent the week since the event reflecting, and pouring over feedback from participants.

I usually define mentoring as a relationship where the mentor does three things for the mentee:

  • Answers questions
  • Provides resources
  • Removes obstacles

These are in order from most obvious to least obvious.

Sure, we answered a few questions based on our collective experience with startups. And we provided plenty of resources: coaches, tools, templates, time, the space, etc.

But all of that is in books. All of that is on YouTube. It’s all… out there.

But good mentorship is about remove obstacles, and 99% of them are self-imposed.

“I can’t do Y until I figure out X,” they say, as they pound their head against the wall of X.

So we just… take X off the table.

Can’t get customers until you have an app? Build a rapid prototype. Can’t market to customers without revenue? Just go talk to them. Can’t get equity investment yet? Get funding from customers.

And it’s like a light switch.

They’d been pounding their head against the wall for weeks and months — some even years — and we just… asked them to take two steps to the left.

Because there’s no wall if you move over here.

The result? We heard from several founders that they made more progress in two days than they had in two years. 🤯

Humbling.

And the event was far from perfect. For Cameron, Laura, and me, it was an experiment. Our own MVP.

We learned a lot:

We had twice as many existing companies as expected, and half as many new companies. We reworked the Friday night plan while it was happening, changed judging criteria in real time, reduced pitch time from 5 minutes to 2 minutes half way throught the weekend, and so on. Ask me and I’ll tell you some war stories.

Honestly — it was a crazy, chaotic, high-energy, draining, and absolutely beautiful hot mess.

We’re going to fix some of the mess for the next one. And, frankly, some of the mess, we’ll keep.

Mess is amazing sometimes.

And in our anonymous followup survey, the average rating from participants was 9.4/10. That’s amazing, and humbling. But… as I said… we didn’t do anything.

All we did was remove an obstacle or two. We took “perfect” off the table. We threw in a couple of constraints. We provided some resources.

But the work? That was 100% them.

That’s the power of mentorship. We just pointed and said, “you’re describing over there but you’re not walking that way.” And the moment we did, they spun on their heels and ran that way.

I’m grateful to have played a small role in the journey of the these companies, and for them to have played a role in mine.

It’s deeply rewarding.

So much so… that I’m doing it again. In October and November, I’m facilitating three more (3 more!) Startup-Challenge-like events across the country — in Los Angeles, Redding, and Orlando. I’m excited.

If you want to get involved in the magic, hit me up. There’s room on the train to join us.

Oh, and before you go — quick announcement:

In just two weeks, I’m kicking off a new cohort program on rapid prototyping, sponsored by the Sacramento MetroBusiness Center — so it’s free to join!

The Traction Thinking Cohort is a 30-day rapid prototyping bootcamp with real-time and asynchronous support that teaches you how to test ideas with real customers — by doing it.

Interested in joining? Apply here →.

Know someone who would benefit? I’d appreciate you pointing them this way.

So yeah. That’s my Q4. Three more competitions, two cohort programs, conferences, speaking engagements, and my day job.

Oh, because I married a therapist, I also have some vacation planned.

What does the rest of your 2022 look like?


When you're ready, there are 3 ways I can help you.

  1. Ask me a question during my weekly office hours  (Thursdays at 11am pst).
  2. Work 1:1 with me to tackle the most challenging parts of the startup journey (100+ first-time founders).
  3. Run a design sprint with your venture-backed startup team to find traction fast (dozens of startups).

Join the cool kids finding traction for their startup.

Each Monday morning, you’ll get one tool or tip you can use to take your product to market and find traction — or fail fast trying.