what it feels like to grow a SaaS to $1M/yr+
And some wins: booking 500+ SQLs per month with outbound, 0->200k ARR in 5 weeks, $250k budget cuts across a portfolio
What a week for the bootstrapped SaaS founders in our mastermind community. I’ll share a redacted, anonymized list of a few of the things that happened (all of the company names and personal details of the mastermind founders are strictly confidential!):
One founder is using highly-orchestrated, AI-executed outbound campaigns to book 500 sales calls per month over email. They’re doing around $2M/yr run rate. I’m kind of flabbergasted since it seems like almost nobody out there is actually doing AI outbound well; obviously, it takes skill and taste in addition to ‘lots of tokens’.
Another has been taking advantage of Claude Code to find budget cuts of around ~$250k/yr, thus far in 2026 alone, across a portfolio of companies, despite flat MRR; good profit gains, but now it’s time to increase marketing and sales output.
Yet another founder of a B2C app fended off a copycat and a cyber troll and grew an app from literally $0.00 in revenue, to an over $200k ARR run rate, in five weeks.
This is all cool stuff. There’s also a lot of more mundane stuff happening, too. Frankly, MOST of growing a SaaS is kind of mundane:
Wildfront as a portfolio overall has been stuck at around 100k/yr run rate for a whole quarter. We’re blocking and tackling to find new influencers to work with on marketing DemandBird, getting new API access from LinkedIn that unlocks meaningful pipeline, managing ViewExport as best we can despite not putting much sales effort behind it, and welcoming 1-2 new members to our founder mastermind series each month.
Two of our other mastermind founders are stuck at around $1k/mo MRR, give or take. They’re on the right track. Doing good things. But revenue doesn’t always come bursting through the door, rootin-tootin like Yosemite Sam. Sometimes it’s hunting and pecking around, doing tough and unrewarding customer development, getting a tip from a peer, and making small wins that - collectively - unlock a bigger prize. Unsexy, for sure. And yet this is the work many of us are doing before we can go riding off into the sunset with our millions.
No matter where you are - if you’re taking a $2M ARR company to $3M and in ‘optimization mode’ on sales and marketing, or if you’re just starting out trying to productize your agency and add a tech layer to it so you can achieve greater scale via an AI SaaS component - the path is similar:
You take a hunch about a product the world might need.
You talk to plenty of customers about that, and run a basic version by them.
If and when you get it right, people start paying you money so you can afford ramen.
Somewhere in between a month and three years from that point, you get to $15k MRR and the lights sort of ‘turn on’.
Stuff gets easier.
You have some cash flow to reinvest.
Then you can run marketing experiments and find the channels that work best for you.
You decide to hire a team member or two.
Hopefully in the process, you’ve learned a thing or two about compliance, finance, bookkeeping, and filing tax returns on time.
Your customer contracts are in order.
You have a privacy policy and enforceable terms.
You find out how to cache AI responses, use a mix of models, and not spend every penny you earn on Anthropic API costs.
Eventually, you kick and scream your way to $1-2M ARR and now you’re a ‘real company’. With 63% net income margins, you’re starting to feel like a pig in shit.
You learn to be an actual CEO, not a faux-CEO on Twitter with no team and barely any revenue (jk, nobody ever does that, right?).
You realize that to build a good company involves being a good leader, not just a good growth hacker and coder.
You have decisions to make: try to sell to PE, or grow more, or maybe wait for lightning in a bottle to strike and have a strategic reach out.
Perhaps you hire a broker at that point to test the market and not leave this process to chance.
Maybe the sale works, maybe it doesn’t.
Maybe you decide, screw acquisitions, I’m going to build a generational company with an ESOP.
Maybe.
The early steps are much clearer, but the later steps… well, it’s impossible to predict the future. After a certain point, with more going on and more money involved, there’s just not one clear blueprint of how to do things. You, your choices, your idiosyncrasies, your goals, become much more important.
I’ve sold a few businesses now. My cofounder Mac has, too. It’s great to sell as a bootstrapper. But if you’re like us, the first thing you want to do…. is get right back into it once the last earnout check clears… or even before it does :)
How about you - where are you in this journey? You read this far, you may as well reply to us and let us know. Tell us what you’re building, what you’re struggling with.
We’d 100% love to hear about it, and give you some feedback if you’re open to it.