Entrepreneurship has taught me a lot. But if I had to boil it down to one lesson I wish I’d learned earlier (and re-learned fewer times), it’s this:
Choose your partners wisely.
Not your vendors, your logo designer, or even your accountant.
Your partners. The people who have access, influence, and proximity to the thing you’re building.
Because here’s what nobody tells you loud enough:
As soon as the business starts working -even a little- people get weird.
Not everyone. Not always. But often enough that you should plan for it like you plan for taxes, cash flow, and the fact that your “quick project” will take 3x longer than you think.
The moment everything changes: you land the “big one”
I remember landing a huge client early on. The kind of win that makes you sit back and go, “Oh… this might actually become something.”
And then the “partner weirdness” started.
- One partner decided that his wife should now be included on the contract. Not because she was doing work. Not because she was required. Just because… now there’s money here, and suddenly everyone wants a seat at the table.
- Another partner invited his buddy to “help with social media.” Seemed harmless. Collaborative. Friendly.
Later we found out that this “buddy” was quietly pitching the CEO to take the entire contract, undercutting our prices, and trying to replace us.
That’s not “oops,” or “miscommunication.” That’s character.
And it taught me something that has held up across industries, across teams, across years:
Success isn’t just a reward. It’s a stress test.
The business doesn’t feel – people do
Here’s the tricky part: business is numbers, operations, and execution.
But people bring:
- ego
- insecurity
- entitlement
- resentment
- old baggage
- friendship dynamics
- family dynamics
- unspoken expectations
So even the most well-intentioned friendships can get strange when money shows up.
I’ve seen partnerships go sideways because someone decided they “deserved more” than another partner because they felt like they were “doing more work.”
Sometimes they were doing more work. Sometimes they weren’t. But either way, if you don’t define roles and expectations early, feelings will fill in the blanks.
And feelings are not a business strategy.
This is why I’m cautious now about starting businesses with friends. Not because friends are bad, but because friendship is built on grace, and business is built on accountability. Those can coexist, but only if you’re brutally clear up front.
Group projects were entrepreneurship training… whether you knew it or not
Think back to school group projects. Same movie, different decade.
There were always a few recurring characters:
- The Natural Leader
Organizes, pushes things forward, takes ownership, worries about the grade. - The Wait-for-Instructions Person
Not malicious, just passive. Will do work if directed, but won’t drive. - The “Sounds Smart” Talker
Great in meetings, big on ideas, light on deliverables. - The Free Rider
Does the least, benefits the most. - The Credit Taker
Shows up at the end and narrates the whole thing like they carried it. - The Chaos Agent
Adds complexity, changes direction late, breaks what’s working.
Adult entrepreneurship is the same set of personalities… but now the grade is your rent.
Psychologists even have a name for the “free rider” dynamic: social loafing, when people tend to put in less effort in a group because responsibility is shared and individual contribution is harder to measure.
Closely related is the Ringelmann effect: as teams get bigger, individual effort often drops.
If you’ve ever felt like, “Why am I doing 80% of this?”, congratulations, you’re not imagining it. That’s a documented human tendency.
Which leads to the next part…
The “Man in the Arena” problem: the doers attract criticism
One of the most useful frames I’ve found for partnership dynamics comes from Teddy Roosevelt’s “Citizenship in a Republic” speech, commonly called “The Man in the Arena.”
A line I come back to often is:
“It is not the critic who counts… The credit belongs to the man who is actually in the arena.”
Here’s why that matters in partnerships:
- The people doing the work make visible mistakes.
- The people not doing the work have extra time to critique.
- The harder you grind, the more surface area you create for criticism.
That’s normal. That’s part of building.
But it becomes toxic when criticism comes from inside the partnership, from people who aren’t carrying the weight, yet feel entitled to judge the people who are.
Look for partners who lift. Not partners who snipe.
Because a business is hard enough without friendly fire.
My first question for future entrepreneurs
When someone asks me, “Do you think I can be an entrepreneur?” I usually don’t ask about their idea first.
I ask:
“What is your work ethic?“
Because a lot of people want the benefits of entrepreneurship:
- freedom from a boss
- flexibility
- upside
- “being their own CEO”
But they haven’t done the math on the trade:
- uncertainty
- long stretches of unglamorous work
- being responsible for everything
- making decisions with imperfect information
- eating mistakes you can’t delegate
If it was easy, everyone would be doing it.
And if your potential partner talks a good game but avoids real work? That’s not a “quirk.” That’s a future crisis.
“Expect it to get weird” is not pessimism, it’s preparation
There’s research suggesting co-founder conflict is a major reason startups fail. Noam Wasserman (Harvard / The Founder’s Dilemmas) is often cited for the idea that a large share of high-potential startup failures involve “people problems” and co-founder conflict.
I’m not bringing that up to scare you. I’m bringing it up to normalize what founders quietly experience:
The partnership is often the single biggest risk factor.
So instead of hoping it’ll all be fine, build like it won’t be, and then enjoy it when it is.
How to vet partners before the money shows up
Here’s what I look for now (learned the hard way).
1) Do they ship?
Ideas are cheap. Execution is rare.
Ask: “What have you built, finished, or delivered -repeatedly- without being pushed?”
2) How do they behave with “access”?
Watch what happens when they get proximity to your clients, your reputation, your network.
Do they:
- protect trust?
- respect boundaries?
- act like a steward?
Or do they treat access like leverage?
3) What’s their relationship with credit?
Healthy partners:
- share credit
- deflect praise to the team
- don’t keep a scoreboard
Unhealthy partners:
- narrate every win as “their” win
- minimize others’ contributions
- become accountants of effort
4) How do they handle conflict?
Ask directly:
“When you’re stressed, what do you become?”
And then watch if their actions match their answer.
One more “tell” I’ve learned to watch for in partners is timing. If an issue happens and someone brings it up in the moment (or soon after) with specifics, “Hey, that client call went sideways because we promised X; can we fix how we’re handling this?”, that usually has legitimacy because the goal is resolution and the feedback loop is still connected to reality. But when a partner sits on something for weeks and then drops it mid-argument, mid-negotiation, or right when you’re winning? That’s often not problem-solving; that’s ammo. Communication research even names this pattern: gunnysacking (storing grievances to unload later) and kitchen sinking (dragging the past and/or conflicts into the present to gain leverage), and both tend to derail the actual issue at hand.
5) Do they lift or criticize?
Every business needs debate. But there’s a difference between:
- challenging ideas (good)
- undermining people (bad)
Put the “prenup” in writing (because memory is a liar)
If you’re building something real, don’t rely on vibes.
At minimum, get clarity on:
- roles and responsibilities (who owns what)
- decision rights (who decides what)
- equity and how it can change (vesting, cliffs, performance-based adjustments)
- what happens if someone leaves (or stops performing)
- client ownership and boundaries
- conflict resolution process
One reason early equity splits go wrong is that teams often lock things in quickly, before reality proves who will actually carry the load.
This isn’t about distrust. It’s about reducing future ambiguity, because ambiguity is where resentment grows.
(Standard note: I’m not a lawyer. Talk to one for the legal structure. But don’t skip the conversation.)
A quick “partner readiness” checklist
If you’re considering a partnership, ask these questions out loud:
- What does success look like for you in 12 months?
- How many hours per week can you truly commit – consistently?
- What are you willing to do that you don’t want to do?
- How do you want to be paid (now vs later)?
- What happens if one of us needs to step back unexpectedly?
- How do we make decisions when we disagree?
- What’s off-limits (clients, side deals, hiring friends, spouses, etc.)?
If those questions feel awkward… good.
Awkward now is cheaper than ugly later.
The bottom line
Entrepreneurship is hard. That’s not a complaint, it’s the price of admission.
The people you build with will either:
- multiply your momentum, or
- drain your energy at the exact moment you need it most.
So choose partners who:
- work
- ship
- protect trust
- lift the team
- tell the truth
- don’t get weird when it starts working
And if you’re not sure yet?
Start with contractors, small projects, and test commitments.
Because partnership is the highest-leverage decision you’ll make, and leverage cuts both ways.
If you want a second set of eyes on a potential partnership structure (roles, boundaries, what to put in writing), I’m happy to help you pressure-test it. This is one of those areas where 30 minutes of clarity can save you 3 years of headaches.
Also read Pullman Doesn’t Need Just One Big Event. It Needs 45 Reasons to Visit.