The accountability experiment

I've participated in multiple accountability groups over the years, from YC group office hours to bi-weekly Zooms with friends to check-ins with my therapist. They've helped clarify my thinking and nudge me toward the right goals.

Accountability groups have been around forever, from Alcoholics Anonymous (AA) to Young Presidents' Organization (YPO). But still, very few people participate in anything structured, especially solo founders.

So, a few weeks ago, I tweeted:

I just wrapped up the experiment, 3,342 text messages later. 12 founders participated and shared their anonymous feedback. It was overall very positive.

Below are my learnings and observations.

1. There’s willingness to pay

Over 200 founders texted me to participate. That was surprising, considering I limited qualification to solo founders in the North American timezone who were willing to pay $100. If everyone converted, that would equate to more than a $500K annual run rate from a single tweet.[1]

But my goal wasn’t to make money. The $100 charge was used to qualify serious participants. It’s also not nearly enough to motivate me financially considering how much time I spent with each person.

Now truthfully, it's not entirely clear if they simply wanted me to be their text message buddy or if they were really driven to find accountability.

But 100% of the founders who participated said it was valuable and wanted to continue. When asked how much they would pay, answers ranged from $30/mo to $1,000/mo to “Name your price” (lol). The average was $300/mo.

The diversity of answers reflects the stage of founders I worked with, which varied from a pre-funded project to a founder generating well over $10M in annual revenue.

2. Not just for the inexperienced

The variety of founders that reached out was also surprising.

Accountability isn't just for the inexperienced, as one might assume. Very seasoned founders reached out, including an early multi-time founder tinkering with a new idea, a CEO that runs a $20M/year bootstrapped business, and an engineer that previously built a unicorn with fresh funding for their new venture.

3. Recruiting was the most common tactical challenge

Every morning, founders shared their #1 goal and blocker for the day. They reported a wide variety of challenges including underperforming team members, lack of growth, technical roadblocks, difficulty knowing what to prioritize, and self-doubt.

But the most common challenge by far (~40% of all reported blockers, according to ChatGPT’s analysis) was in recruiting. This included full-time hires, contract talent/agencies, and a cofounder. This isn’t too surprising – it mirrors what I’ve seen in the hundreds of investor updates we receive at Weekend Fund.‍

4. There’s value in having an outsider on your side

It’s very common to have doubts and feel lonely as a founder, especially when solo. The founder is supposed to have all the answers. Showing weakness to the team or investors can be risky. That’s very hard and isolating.

An outside party that doesn’t have a direct stake in the success of the business can serve as an outlet for honest conversations and unique perspective. A few of the founders who participated echoed this sentiment when asked what they found most useful:

“The practical advice and referrals I really liked! I also felt validated and less alone, especially as a solo founder.”

“As a solo founder, you often face prolonged periods of feeling down, which you can't share with your team without impacting their morale. Morning messages from Ryan are comforting because he genuinely wants to hear my thoughts and responds when he can add value.”

“Having someone checking in on me that operates from a different altitude.”‍

5. Most importantly, founders liked the music recs

Every morning, I shared music that I enjoy. This included calming handpan music, deep house mixes, and a new album from an artist I love.

No one hated them! Success. :)

So, what’s next?

This initial experiment was (intentionally) unscalable. The $100 I charged per person was purely a filter and not a means to generate any meaningful revenue (I estimate my hourly rate backed into $40/hour).

But I learned a ton, and that was the goal.

There’s clearly demand for something like this, which could take many different form factors to scale:

• ‍100% AI. LLMs have passed the Turing Test, but would someone feel accountable to an LLM? Maybe. Here’s a recently launched app for exactly this.
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• AI + Human. AI tooling and a human could be a magic combination. AI can drive more efficiency and potentially better results while the human primarily serves as an important ingredient to remain accountable. System2 builds tools for fitness coaches to scale personalized guidance (we’re an investor at Weekend Fund).
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• Peer-to-peer. I’ve always been a fan of community-driven models, which shouldn’t be a surprise considering my Product Hunt experience. When done well, they can provide better results than 1:1 models, scale infinitely, and help with distribution through WOM. Buildspace is an excellent example of this (we’re an investor at Weekend Fund).
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• Combination of the above. And of course, one can apply a mixture of all of the above.

At the moment, I don’t plan to pursue any of these. I could make a good amount of money scaling this, but I’m not particularly drawn to do so. Instead I’m prioritizing things that spark my curiosity and sound fun, because the opportunity cost is high.

Onto the next experiment, and if you’re interested in following along, subscribe here. :)

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[1] Of course, not everyone would convert or retain, but this shows there’s demand for something like this and with a little more effort, I’m confident I could 10x top of funnel quickly.

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