Happy holidays everyone!

This will be my last newsletter this year, so I’ve added a few more personal touches towards the end of this letter. I hope you like it.

Here’s what I’m writing about today:

1. Results and takeaways from entrepreneur collectible cards
2. Saying “Your jobs are safe” then immediately firing someone
3. A collection of topics from our peer groups conversations
4. 2 member tactics for buying businesses
5. Reverse Survivorship bias
6. A personal thought on Legacy
7. Vanlife update
8. What I’m thankful for

I wanted to follow up from this newsletter I wrote last month.

The cards were a smashing hit, but I would not say they were a smashing success

Here’s the results:

Measurables:

Immeasurables:

Adam Hassan said one thing specifically “You mastered everyone’s favorite subject… Themselves.”

Thank you Adam

So did it drive enough immediate business to justify the cost and effort?

Not even close.

But was this test worth it?

I think so.

The fact is that right now we have a compelling ice breaker. It’s something that opens the door and gets us a conversation, which is often the hardest part of B2B sales, especially with a discretionary service like ours.

So right now we’re going to work this into a specific marketing strategy and experiment with it another 2-3 times in 2026. The strategy is basically just decreasing the cost of producing these cards and targeting our ICP at a significantly deeper level.

One of our members recently bought a second skilled trades company doing ~$4M in annual revenue.

Before he acquired it, he built a strong relationship with the owner, went deep to really understand the employees, he even had the seller fire one bad apple before the acquisition happened.

Then he walked in with his announcement speech and said, “don’t worry, all your jobs are safe.”

Well, then he sits down with one of the managers who has a horrible attitude and recognizes this person needs to go.

He comes into our peer group and asks, “what do I do about this guy?”

Another thing to consider: this manager is going to have surgery soon which means he’ll be missing work and will have some recovery time.

If you haven’t realized this already, this could turn into a painful lawsuit if he doesn’t handle this situation properly.

The first thing to say is that he wanted to stay true to his word, he really meant it when he said that everyone’s job is safe. He just didn’t expect this to happen immediately after buying the company.

The second thing to say is that I’ve seen a similar situation before. One operator’s technician was injured on the job, had a reduction in hours post-surgery for recovery. The problem was that this technician was harassing other employees in the office and the other employees waited to come forward about these issues until he was in recovery. So the owner asks an attorney for their advice on firing someone during this recovery period and discovered there’s a 99% chance the technician wins the case and it costs $1M+.

So our feedback to this owner was to

1. Talk to an attorney immediately

2. Understand it could be months before this employee can be fired, and although it’s a bad look to “go back on your word” it’s probably best to let the person go immediately. Tradeoffs, tradeoffs, tradeoffs…

One of our members is negotiating a new equity partnership, and he came to the group for help.

The short part of the story is that he found a local experienced operator who built several businesses through partnerships and had some 8 figure exits. Our member has a high degree of certainty that this person will be able to help him grow. So he’s going to give him a smallish percentage of equity to incentivize this operator to help the company grow.

Jackpot, right?

Well, we had a conversation on how to protect yourself as an operator considering granting equity to a new partner, because we’ve definitely had a few horror stories where partnerships have blown up in people’s faces.

Here’s a few things to watch out for:

A. The messy middle problem

Most of the time you hear about business partnerships, they are usually amazing success stories, or absolute disasters.

From my experience and from our members, it’s more likely that your business partnership ends up somewhere in the middle. Where some elements of the partnership go very well, and other elements need improvement via difficult conversations.

You can and should create legal documentation that prevents worst-case scenarios, but you should also prepare for how you’ll handle gray area issues, and create a plan on how to handle difficult conversations with someone you’re married to (business marriage).

One member’s advice: "Communicate roles and responsibilities and expectations and document them. Have a frank conversation about what happens if it's not going well. Here's how we'll measure it and here's what we'll do."

Get ahead of those difficult conversations and mutually plan on how they’ll be addressed.

B. Time commitment

I suggested quantifying a business partner’s time involved in the operation. If a potential partner says “this will be my main focus” ideally there is a number attached.

I mention this for 2 reasons.

- I know 2 business owners whose partner’s stated involvement was significantly less than what reality turned out to be. Both times resulted in ugly buy outs.

- Entrepreneur-types can get bored easily, you don’t want someone getting equity and working hard just to switch their focus 6-12 months down the line, now with equity in your company.

Write down the minimum time commitment. Not "this is your main focus." Actual hours.

C. Who's actually driving the results?

Another member pointed out a structural flaw: "Be aware of the results you’re looking for from this person and what the drivers of those results are, quantify those KPIs because you could end up doing all the work to hit that number and open the door for him when you could have just done it yourself."

Just because equity vests at $5M revenue doesn't mean the partner contributed to hitting that number. 

D. Working styles

One member wished he'd understood his partner's working style before jumping in. "Me and my partner are actually both very similar and sometimes I think I could really use someone who's the opposite of me."

They're aligned on values and goals. But their similar working styles creates friction in unexpected ways. When conflicts emerge, you need to understand their natural tendencies, not just their skills.

Nobody in the group told him not to do the partnership. Nobody said partnerships are universally bad.

Instead, everyone shared where they got burned, and what they would do better the next time so he could avoid those problems.

Look, I wrote out a lot of this, then deleted it, then added it back in, then deleted it.

My outlook on the search/ETA ecosystem is that it’s more competitive than ever. PE is far down market, every bizbuy sell listing >$500k in ebitda gets 100+ of CIM requests, every publicly listed deal will have at least a few legitimate buyers you’re competing against. Prices/terms have shifted in favor of the sellers out of a result of this market demand.

I’m hesitant to give advice on buying companies because I’m not an expert myself, there’s a ton of caveats, required context, and “it depends” applies to everything.

That said, I talk to a lot of people in our peer groups smarter than me, and I hear about what they’re doing that is working, so here’s a couple tactics you should take with a grain of salt:

1. Buy companies no one else wants to buy

When you look at companies no one is looking at, the prices and terms change significantly in your favor.

One of our members does exactly this. The niche he’s in is very cyclical and risky, so he’s got very little competition even in a major market.

His prices and terms are radically free of risk. No SBA debt, no seller debt, no debt whatsoever, small portion of cash to acquire hard assets he could liquidate if he needed to, and pays the sellers a small percentage of revenue over 10 years up to a capped dollar amount worth ~3X ebitda. If revenue declines 70%, he’ll have to make layoffs and sell some assets, but he’s not going to go bankrupt.

Overall, if you can find businesses that don’t have much of a buying market, sellers have to seriously consider your offer. Or they’ll just close down.

2. Put deposits down

Buyers hate it when brokers ask for buyers to put deposits down. They’re probably right to dislike it. But 2 members of ours have offered to put deposits down just to show they’re serious and it’s totally worked to put them above other serious buyers. If SMB M&A still remains competitive for the coming years, I bet

This idea has come to my mind a few times this month.

Survivorship bias is the idea that we get exposed more to and learn the most from the stories of businesses that succeeded and assume their playbook is what drove the outcome, while ignoring the many others that followed the same plan but still failed.

Reverse survivorship bias is the opposite, we get exposed to all the big “loser” stories and ignore everyone else succeeding. I think PE is a decent example because anytime a big PE rollup goes bust, we all hear about it and how stupid the operators are. It makes me wonder, for every PE bust, how many are doing great? In SMB land everyone hates PE, so I think I get exposed to a lot more of the bad outcomes rather than the good ones. No one celebrates PE rollups.

So what’s the point?

My big takeaway from this is to pay close attention to the information you consume. Understand why you’re being exposed to it in the first place, and take everything with a grain of salt. When someone says “You should do X because of this other company that’s succeeding by doing it.” Just recognize that you’re missing a significant amount of information.

Here’s an example from my life:

One of my members told me I should run facebook ads for Scalepath because Somewhere was doing it. But I remember a podcast from Jon Matzner where he says that Somewhere is failing at FB ads and always has to go back and lean on Nick Huber’s twitter to grow the business.

So what’s the truth? The reality is somewhere in the middle, and it’s a much better activity for me to look at every step in my customer acquisition process and understand what needs improvement.

What’s our ICP?
Which channels get us in front of them?
What messaging will most resonate with them?
What do we say on the first discovery call?

At this moment, breaking down our strategy and thinking deeply about it is probably a better use of time than just yeating money into FB ads.

And at the very same time “just take action.” is a great rule of thumb to prevent us from over thinking.

But I already did that with cold email, I moved fast, spent some money and ultimately discovered our lack of intentionality was getting us leads outside our ICP who weren’t great fits.

And as I described above, our first test with the card game didn’t drive an adequate amount of revenue to make up for it. So do we just stop and say “it doesn’t work, move on?” or do we take one of the other 20 levers to pull on (in this case, targeting our ICP more narrowly) and improve the overall process?

So my point is that you should be intentional about which experiments deserve iteration versus which deserve burial. The card game didn't hit revenue targets, but we saw tremendous success in opening doors and building relationships so we're iterating with tighter targeting. Cold email got wrong-fit leads and is very challenging to find our ICP as narrow as we need to, so we buried it. Sometimes "just take action" is right, sometimes "move intentionally" is right. The skill is in taking in all the information you can and adapting it for your unique situation.

I’ve had moments of jealousy looking at other people who grew up in entrepreneurial families.

They just seem to succeed earlier, quicker, easier, and with more success than those who didn’t come from an entrepreneurial family.

And when I say “entrepreneurial family” I generally mean basically any business with at least a handful of employees.

Also, I’m not talking about people who had inherited a business or a cash flowing asset, that’s not where this comes from. It comes from people who simply got a lot of exposure to entrepreneurship, simply noticing it as a viable path from a young age versus someone like myself where I basically learned about it when I was 21.

First, I vulnerably say this because I recognize that it’s a stupid way to think. There’s nothing I can do about this, it’s a worthless thought. It’s just one of those thoughts that comes into my head a few times a year. I quickly recognize that it’s not valid, not worthy of consideration, and an unhealthy practice of envy.

“Boohoo, someone was dealt a different set of cards. What can I do about it? Nothing? Okay move on.”

But, it did make myself think about the kind of values I hope to offer to my future children.

Which brings me to the topic of leaving a legacy.

What do you think the definition of legacy is?

If you asked me 5 minutes ago, I would have said something like “a list of accomplishments one earned through their life” or something about doing a lot of things or building something that others consider admirable and exciting.

But here’s a couple definitions:

Google says: “the long-lasting impact of particular events, actions, etc. that took place in the past, or of a person’s life.”

Okay, I guess I was kind of right.

But I prefer Chat GPTs answer:

“The impact, values, lessons, or reputation a person leaves behind.”

I love that so much more than how most business owners talk about leaving a legacy.

When most business owners talk about leaving a legacy, it usually mentions building a big business, creating generational wealth, and being the person who set their family up for a life significantly better than they had.

All positive things! I resonate with a lot of it. But I do think that the impact, values, and lessons, and tools you give your children vastly outweigh any monetary amount you can pass on to give them a head start.

(please forgive me as a single man speaking out of my depth, I know how this sounds).

But despite not growing up with much, I think my parents did a really good job instilling values for myself and my brothers, and we can take all these subtle lessons our parents taught us growing up and be successful in practically anything we want to do in life.

Now it’s up to me to iterate and improve on those values, and pass them on. That will be far more meaningful than any form of inheritance.

The events are cool, van life is cool, but it’s wearing me down.

I did ~7 months from September 2024 to April 2025, and another 2 months from September 2025 to November. I’ve also had ~7 weeks of shorter 1 week trips during that time.

Technically, I’ve saved ~$32,000 on AirBnBs/hotels by traveling in a camper van, all while getting to travel the country and hangout with awesome people, many of whom I consider friends that I would not have otherwise built as strong of a relationship with.

But there’s a few things that just wear me down.

- always making new decisions on where to work, sleep, eat, workout, people to see, etc.
- doing all of these events generates a lot of new tasks for me, which means that my day to day gets significantly busier.
- I think there’s this invisible “hum” of instability and lack of safety that comes with van life. I don’t feel it at all but I think it exists.

All of this is causing me to be far more intentional with my travel, and limit it to 1-2 months a year.

I still like the van, it’s an awesome tool especially for trips ~5-6 hours away from NE Ohio where I live. It’s served a lot of its purpose and I expect how I use it in 2026 will change significantly.

I’m writing this portion of the letter the day after Thanksgiving.

Last night, I spent 9 hours with my buddy Sam Dempsey who I met at an Akron SMB meetup ~3.5 years ago.

This Thanksgiving, he invited me into his family home to eat dinner with ~12 of his family members.

I’m in Ohio, I have no family here, in past thanksgivings I have been alone. Previously I thought I was strong to not need to have others, or that a holiday is just any other day.

I think I was wrong.

Over the last few years during my travels, many people have brought me into their homes, gave me a place to sleep at night, and it’s been one of my favorite things I never expected to love.

Traveling as much as I have been has been exhausting, and now anytime I’m fortunate enough to be brought into someone’s home and treated like family has been so tremendously meaningful I really don’t have the words to express it.

So thank you to these people:

John Wilson for countless pizza, wings, and giving me the first mattress I slept on when I moved to Ohio when I knew no one.

Preston Holland who was the first internet stranger who gave me a guest bedroom for a night on a random road trip

Rory Tyer and Heather for many breakfasts, dinners, a spare desk in your office, and chasing backyard chickens with your family.

Jack Carr for taking me in when I first bought the van during one of the worst weeks I’ve had over the last couple of years.

Aaron Harper for leaving me his home for a whole week.

Michael and Amy Nieman for staying in your home for multiple months, and thanksgiving last year.

Sam Dempsey for thanksgiving with your family last night and a strong friendship

Kevin Henderson and Craig Marquis for hosting me in your office for a whole week

Tom Dillon for letting me sleep in your spare bedroom on road trip to Chicago

Michael Reardon for letting me sleep in your guest bed when I was passing through Milwaukee.

Brandon Niro for several nights on your couch and guest bed

George Tibil for a late home cooked dinner that one night

Brennan Wyatt for a few days during my stay in Toronto

And to everyone who's opened their homes and places of work to me along the way - you've made this whole journey so, so much more memorable and fun. I'm forever grateful.

Talk soon,

Rand