If this year has you feeling a bit isolated as a bootstrapped founder, you’re definitely not alone. Even though I’m always going to be all in on remote work, 2020 is really putting the emphasis on the “remote” part. 

And most of us know that bootstrapping could feel isolated even when co-working spaces, spontaneous coffee meetups, and in-person conferences and events were a thing. But we can’t just put our businesses on hold until things are “back to normal.”

So what do we all do until then to keep improving our businesses, and building our networks with people who are facing the same challenges we are? We create community where we can. And right now, that’s online, so that’s where we are with Founder Summit.

Back in March Tyler Tringas and I were over the moon about the idea of bringing founders together in Mexico City to develop lifelong connections over Mezcal toasts and battling luchadores. It was a heart-wrenching decision to call it all off, but in hindsight, we definitely made the right call. All these months later, I’m so impressed with where we’ve wound up after pivoting to an online community, and I couldn’t be happier with the conversations we’re having and the connections we’re all making. 

We’ve grown to 200+ founders and we’re learning from each other and improving all the time.

Over the past several months, our co-working sessions have been such a hit that we’re going big and kicking off a Mastermind Sprint in October with 8 full weeks of structured deep dives with a cohort of founders at your level, plus a mentor who’s seen some sh*t.

The goal of the Mastermind is to help founders crush their next milestone with: 

  • Accountability from peers 
  • Insights from mentors
  • Momentum from sprints

I can tell you from personal experience putting a similar system to work on our 30+ companies at SureSwift that this kind of focused and time-boxed effort makes a huge difference, whether you’re trying to launch your company or you’ve already been in business for years.

I’ll be participating as a mentor, along with Tyler, and others like Michele Hansen, CEO of Geocodia, Ben Tossell, founder of Makerpad, SureSwift alum and serial entrepreneur Matt Stubbs, and others.

We also just announced a bunch of  new talks, panels, office hours, and remote co-working sessions for fall. 

Member Bridget Harris just led a “Things I’ve Learned” session this week on pricing her freemium SaaS, You Can Book Me, which she bootstrapped into a multi-million dollar company that generates 1,000,000+ bookings a month. (Pretty cool when a service many of us have used at our own companies was started by a fellow bootstrapper! New members can catch Bridget on a recording.) 

Member Austin Gray is leading 3 virtual co-working sessions this month as part of his work with Productive Cycles and Startup September

Every month we have 3-4 founders sign up for our “Sh*t We’re Working on” demo day (I guess we say sh*t a lot. Don’t tell my kids). This month we’ll be checking out what Ward Sandler from Memberspace and Jon Fry from Lendflow.io are up to.

Every month now we have 3-4 founders sign up for our “Sh*t We’re Working On” demo day (I guess we say sh*t a lot. Don’t tell my kids). This month we’ll be checking out what Ward Sandler from Memberspace and Jon Fry from Lendflow.io are up to.

Tyler Tringas on Twitter sharing demo day from Founder Summit Remote.

We have (virtual) mingling and mezcal, too.

We’ll be keeping it fun along the way, too. Our community lead, Najva’s Giphy game is on point. We have a quarterly happy hour on top of all the learning and doing. And because Founder Summit is invite-only, we’re able to keep it an ego-free place where a founder who’s working on their first startup can rub virtual elbows with founders who are bringing in millions in revenue. 

That’s one of my favorite things about the bootstrapping community. Of all the types of entrepreneurs out there, I find bootstrappers are the most down-to-earth, been-there-before, people-I-actually-want-to-have-a-conversation-with. 

So until we can all meet up over tacos and beers for real, if you’re interested in joining us for the sprint in October, or for the community in general, it’s a good time to apply. The cost is $199 for an annual membership (our goal isn’t to profit, just to cover our costs), and we’re getting ready to send out a new batch of invites to a select few new founders before the Sprint starts in October. Hope to see you there.

Join the Founder’s Squad

Founder stories, advice and case studies.

You have successfully subscribed!