Flywheel 😶‍🌫️

Hello old friend.

It’s been a minute.

I’ve been heads-down building, plus doing some big-picture thinking about FFSR (more on that in the next one). Last post (Reverse Engineering the Ideal SpeedRun SaaS), I promised a deep dive into my new SaaS, Flywheel.

Here it is.

Lock in.

At some point in the life of most software companies, they reach a stage where reducing churn & increasing expansion revenue becomes one of the most viable growth levers. In some cases its because they hit a churn wall, where they are loosing revenue to churn as fast as they are adding revenue from new users, causing growth to plateau. In other, albeit rare, cases, its a result of market saturation: these companies simply begin to run out of potential customers.

At this moment, it becomes incredibly prudent for founders/operators to look inward, and ask the question: how do we earn more from our existing customers?

Flywheel aims to assist companies when they reach this juncture, or to prevent them from ever hitting this wall in the first place.

So what IS Flywheel?

Flywheel is an event driven customer communication platform that helps SaaS companies boost their net retention rate. It helps them keep more revenue by reducing customer churn, increasing activation, and boosting satisfaction. With Flywheel, companies can create advanced email and slack workflows to activate customers more effectively, increase their LTV, and reduce churn.

So Far

Here’s the rundown on what’s live and kicking—and how it’s helping SaaS teams print.

The most cracked Workflow Builder You’ve Ever Seen

• Plugs straight into Stripe. When a user subscribes, upgrades, downgrades, or cancels, Flywheel fires off emails or Slack messages like clockwork. No more “oh crap, we forgot to follow up” moments—keep users engaged and churn go 📉.

• Hooks up with PostHog and Segment (more integrations dropping soon). It grabs the events you’re already tracking and lets you trigger automations off them. Bonus: it syncs your event schemas, so you can slap user-specific details (like “they used X feature 5 times”) right into your emails. Activation? 📈.

• Spits out gorgeous, minimalist, marketing emails by default—no design degree required.

• Lets your team send one-to-one emails or Slack pings to any user. Personal connection = happier customers = more revenue sticking around.

User Profiles That Don’t Suck

• Flywheel auto-links Stripe data, event history, emails, and Slack chatter to each user. No more juggling separate email lists—your user list is your email list. This means you’ve got every user’s subscription status and app behavior at your fingertips. No manual syncing, no data gaps. You can hit them with the right message at the right time—think “Hey, you’re killing it with [feature], want more?” Expansion revenue go Brrrrrrrr.

Admin Tools That Free You From Support Hell

• Back in the early days of Drippi, I was the bottleneck—support would ping me: “add 500 AI credits for this user,” and I’d have to raw dog the prod database to make the change. Eventually I built some quick HTTP endpoints to speed it up, but I was still the only one could use them. Flywheel fixes that.

• It’s got a slick UI where you can spin up custom admin HTTP endpoints for your team. Now your support crew can handle common requests—like tossing credits or tweaking settings—without bugging you. Faster help = happier users = less churn. (And more time for you to function with Latinas)

Whats next?

Stage 1: The best email automation tool in the game - Ops are cooked

The current landscape of email automation tools leaves much to be desired. Both Customer.io and Intercom's workflow builders are clunky piles of shit. And even modern startups like Loops haven't really innovated on anything (besides the landing page maybe).

In an ideal world:

• You don’t have to manually sync customer properties to your email list with API calls.

• Triggering emails based on stripe events shouldn't require building a custom webhook handler.

• You can be segment your customer list with natural language.

• Your email subject lines A/B test themselves

  
  This is the world I'm building.

Stage 2: Build what the fuckin users ask for I guess.

The vision

Software will become largely commoditized over the next decade, and the rules are getting rewritten as I write this. B2B SaaS giants have leaned on economies of scale for 20 years, but their moat is drying up as AI makes building software dirt cheap and 5x as fast. Niche players—small teams with laser-focused tools—are gonna carve out sub-sectors from the old guard’s customer base. Meanwhile, with software itself becoming commoditized, users will demand more—top-tier support and service to seal the deal.

Flywheel is built to ride both trends:

• Bottom-Up Takeover: The big customer communication platforms chase 50+ employee companies. Flywheel is for the $20K MRR+ startups—new entrants who will grow into tomorrow’s giants. We’ll hook them early with better user experiences than the incumbents, cutting churn and juicing activation. With AI sparking a flood of fresh SaaS players, every 50-person team starts small—and we’ll own that pipeline from the jump.

• Vertical, Not Horizontal: Most players sprawl across industries, diluting their message and bloating their products. Flywheel will focus tightly on SaaS customers and expanding by stacking tools that align with their evolving needs, rather than sprawling across industries. We’re considering options like a CDP, revenue attribution, analytics, affiliate setups, or agent workflows, but these are just loose ideas for now. Ultimately, we’ll build what our customers demand, leveraging infrastructure designed to be flexible, drive expansion revenue (think $2,000+ ARPU), and create stickiness—making switching a pain(in a good way) and keeping churn low.

The vision’s straightforward: a platform that’s dead simple, keeps your revenue climbing, and built SaaS founders I’d get a beer with. No platform risk, just a lean retention beast that helps niche SaaS teams differentiate with killer support and service while the old giants scramble.

The Plan

Last quarter’s goal was $5K MRR, but i fell flat—way off the target. We’re still hovering at $200 MRR. The culprit? A myriad of personal failures, mostly tracing back to me sidestepping the obvious plays that landed Drippi’s first customers.

I tried spinning up an agency-style offer to collect some quick cash. It flopped. Lesson learned.

This quarter, I’m stripping it back to the raw, scrappy basics that worked for Drippi: get people using Flywheel, period. No fancy detours, just straight-up traction.

Tyler Denk dropped an absolute heater a few months ago (https://mail.bigdeskenergy.com/p/traction) on wiring up a traction operating system, and it’s been stuck in my head ever since. I’m currently riding solo on Flywheel and there are certainly no imminent plans to establish a “Leadership Team”. Even so, there’s no better moment to start build good processes.

Go check out Traction if you haven't read it. I’m not rehashing it here, and the next section’s gonna be gibberish without it.

• The 5-Year Target: $20M ARR
  Big, bold, and in our sights. Flywheel’s gonna be the lean, mean retention machine SaaS founders can’t quit.

• 3-Year Picture:
  $3.3M ARR. That’s $277K MRR, with 554 customers at $500 ARPU—or 277 at $1K. Niche SaaS teams hooked early, growing with us, and sticking around because switching sucks (in the best way).

• 1-Year Plan:
  $500K ARR. $42K MRR. 84 customers at $500 ARPU—or 166 at $250. Small, scrappy SaaS startups piling in, hooked on dead-simple tools and support that actually delivers.

• Quarterly Rocks (Q2 2025):

  • 50 companies firing off emails with Flywheel, no fluff—just results.

  • 2 podcast episodes a month, keeping the buzz alive.

  • 5-10 signups a day by June’s end, stacking that pipeline from the ground up.

• Scorecard:

  • Net new MRR: $1,350/week

  • Signups: 35/week

  • Podcast impressions: 1,000/week

  • X impressions: 50K/week

  

  It’s all live on my new personal site (https://open.jaen.app)—go peek. Right now, we’re bleeding red across the board, but that’s the point. Turn this into green by Q2’s close, and we’re locked on the 1-year target.

It feels good to be back in the trenches, building from 0, riding sol-dolo, Latinas fading in the rear view mirror, autopilot destination set for $100M in the bank.

thats it for now.

thanks for reading

catch you in the next one. 😘

P.S. if you run a SaaS company, and want to give flywheel a try, just reply to this email and I'll hook it up.