Yesterday I shared (see here) that I conducted a condensed onboarding session for new members joining the accountability group I put together for entrepreneurs. I wasn’t sure how effective that session was, and I hoped that the meeting with the full group would provide clues concerning whether I missed the mark.

Today we had the full group meeting. It was the first time the new people and existing members had met. I adjusted the agenda to include member intros so everyone would have context on the new members and their businesses. Otherwise, it was a normal meeting.

During the meeting, I tried to gauge whether the new members were prepared, engaged, in sync with the flow of the meeting, and net value additive to the group. To my surprise, they met all those criteria. For the most part, I couldn’t tell a difference in those areas between new and existing members.

My takeaway is that the condensed onboarding of new members worked. Of course a few things could be tweaked, but overall, it went smoothly. I think I’ll keep this in my toolkit.

One of the things I’m working on for the new accountability group I put together for entrepreneurs is the process for onboarding new members. I’m adding a few new members to an existing group, and I need them to come to the next meeting ready to contribute and knowing what to expect.

I set up a mini onboarding and workshop meeting with the new members. I went through what makes the group work, what tools we all use, and what’s expected of them as group members. We then did a hands-on workshop where I explained the prework they need to do before each meeting and how to use certain tools to complete the prework. We then completed part of it as a group. I gave feedback and helped them understand how to complete the prework to the standard of the existing group members.

That meeting went well. They said they have a better understanding of what they need to do and how they should go about doing it. But the real test will be the next meeting with the full group. If I did a good job, it won’t be noticeable that we have new members. If I didn’t, I’ll need to refine the onboarding process a bit.

When I was part of an EO forum, one of the hardest things for our group to do was coordinate calendars. We had several busy CEOs with packed schedules. Finding an open time for a four-hour meeting was a challenge. With the accountability group for entrepreneurs I’m spinning up, I’m booking six months of meetings during our first meeting. Everyone opens their laptop at the end of the meeting, and we confirm dates then and there. I send calendar invites that day, and the meetings are locked in.

This worked well until this month, when several group members had conflicts. We needed to reschedule. One of the group members owned coordinating the change, but it dragged on without everyone settling on a date. I jumped in and will pick a date. Likely everyone won’t make the meeting, but a decision needs to be made soon; otherwise, we won’t meet in October.

Coordinating with several CEOs is hard. My biggest takeaway is that inside of 30 days, it becomes many times harder. If a meeting date must be changed, it’s best to do it 45–60+ days out and have everyone agree to the date in person during an accountability meeting.

In the past week, I’ve talked with two unrelated people about their experiences at their prior employers. Both described a feeling of dread on Sunday nights and hating team meetings with company leaders. They went into detail about each company, but the bottom line is that both companies had leaders who didn’t value their employees. They viewed everyone as replaceable, which created a terrible culture. Both companies experience constant turnover, which impacts them negatively in a variety of ways.

Company culture is one of the most important competitive advantages. It’s available for all entrepreneurs to leverage, but most don’t. Hence, the companies that do take advantage of it enjoy massive advantages.

When you create a culture where people work hard but enjoy their work and genuinely like their coworkers, positive effects compound. The company attracts A players, and they usually know other A players, so recruiting is easier. People don’t leave companies they love, so companies with great cultures enjoy low turnover. This helps maintain institutional knowledge and keeps people costs low (it costs a ton to find and onboard a new employee) and productivity higher (new people usually aren’t productive for a few months).

Both of the people I talked with (A players) are now evaluating new opportunities, and they both said something that stuck with me. They’re considering only companies that have great cultures and will work only for leaders who live the values they’ve set for their teams. I’m excited for them, and I’m sure they’ll find exactly what they’re looking for.

Today I met with an entrepreneur interested in joining one of the pilot accountability peer groups that I’m starting. He’s five years into his business, and it’s beginning to grow rapidly. He wants to learn from other entrepreneurs who are also running high-growth businesses, but it hasn’t been easy for him to find and connect with such peers. Therefore, what the peer accountability groups offer immediately resonated with him.

My takeaway from this conversation is that people like this entrepreneur want to connect with and learn from peers. The demand is there for these types of groups.

I’m creating the next set of accountability peer groups for entrepreneurs and have spoken with several strong entrepreneurs. I’m using revenue as a proxy for product–market fit. Basically, if you have over $1M in revenue, you likely have product–market fit. It’s not perfect, but it’s a simple and easy filter everyone can understand.

I’m seeing a difference within the group of entrepreneurs who have product–market fit. Two companies can each have $2M in revenue but be at different stages. For example, one might have had $1M in revenue last year; the other, $2.25M. They will be dealing with different challenges. And they might have different objectives. One may be focused on rapid growth and the other on maintenance and profit harvesting.  

Given this difference, I’m now thinking that my initial conversations with entrepreneurs should include understanding their revenue for the last few years so I can determine their growth rate. I can then ask questions about how they feel about that growth rate and what help they want from their peers (if any) in changing it.

I’ll think about this more and discuss it with others, but understanding historical growth rate might help as a filter and in matching like-minded entrepreneurs.

This week, I met an early-stage software entrepreneur who’s grown his revenue from $400k last year to about $2.5m and intends to close the year at about $4m. That’s about 6x so far this year and around 10x at year’s end. What’s the secret to this hyper growth?

The most important thing is a great software product. They’ve iterated over the last two years and finally found something that resonates with customers. The big unlock was social media marketing. They’ve been using a strategy that involves paying an army of smaller creators for content, then repurposing it as paid ads across social media platforms.

The idea is to get as many shots on goal as possible so you can find the handful of videos that have viral potential. Once you find those home-run videos, you run them as ads with a ton of money behind them. Of course, you have to run the numbers to know your customer acquisition cost, payback period, etc.

I really like this strategy, and I think it’s worth studying for entrepreneurs who are selling products or goods to individual consumers online.

A few years ago, I shared the power of sending update emails with the founder of an AI start-up. Shortly after that, he began sending updates to investors and supporters. I was included on the list, and even though we haven’t chatted in over a year, I’ve been following his progress closely.

This week, he sent an update notifying everyone that he’s shutting down his start-up. His reason is that the market he’s in is too competitive and consolidation has begun. Everyone is building essentially the same AI product, so I’m assuming margins were either not great or nonexistent.

This founder raised seven figures of venture capital. Interestingly, he’s shutting the company down with tons of cash in the bank. He has $1.1 million in cash, but instead of burning through it in a hyper-competitive market, he’s returning it to investors. He plans to work on something more promising.

I’m sure there’s more to this story, and I’ll reach out to the founder. My gut tells me that he’s optimizing for the best and highest use of his time in his prime years and concluded that his start-up isn’t the best use of his time anymore.

I’ve been working to create accountability groups for entrepreneurs in Atlanta. Two have gotten off the ground and are serving as great pilots to learn from. I’m looking to launch a third, but I’m starting to think that coordinating three-plus groups might require me to change how I handle the things I need to do between meetings. Email and text reminders need to go out to founders, and other tasks include agenda prep, scheduling one-on-one meetings with group members, and researching topics that came up and sharing that information with the group.

I don’t love this kind of work, but I’ve noticed that the more organized I am (or appear to be) and the more smoothly run the meetings are, the more prepared and engaged the members are before and during each meeting. I need to find a scalable way to handle all this stuff. If I don’t, the quality of the meetings could be affected.

I don’t want to hire anyone because I don’t want to manage anyone. Instead, I’m thinking about using AI agents to do these tasks or make it easier for me to do them. I’m going to do some digging. I think this could be a great excuse to test some of the newer tools: Grok Bot, Muse, Instinct, etc. I’ve been wanting to play with these, and this use case might be the perfect way to learn how to use them.

This week I got to attend a celebratory dinner for a founder who just sold his company. It took six months of grueling work to get the deal over the finish line, but it finally closed. The founder was noticeably exhausted, but he made a point of celebrating this deal with his team.

The experience was a reminder of how important it is to celebrate wins with everyone who supports your journey or is part of it.

I’m happy for this founder and glad I got to celebrate with him.