A friend of mine, Haley, spent 15 years working in a lot of bad cultures. Some mildly disappointing, but some actually bad. Really bad. So by the time she was interviewing for her next job, she had one non-negotiable: the culture had to great and it had to be real.
Haley told her potential employer this upfront, “I’ve been around long enough to know what bad looks like and I’m not doing it again.”
Her soon-to-be new boss told her they were really proud of their culture. That it was one of the best. That it wasn’t a branding exercise, it was real. So, she did what any smart person would do. She talked to people on the team when the boss wasn’t in the room. She said everyone told her the same thing. The flexibility was real. The support was real. The expectations were high but fair, and they were happy to be a part of the team.
She was genuinely excited and said for the first few months, it was everything they said it would be.
Then, things ACTUALLY got real. She explained, “The blend of in-office and WFH I was promised turned into five days a week in the office. I wasn’t supposed to work on weekends, but it slowly evolved into working most evenings and weekends. The technical manager was fired, and his workload got handed to me, on top of the job I was hired to do. Without a conversation. Without a title change. Without additional compensation. And when I finally told him the workload was too much, he told me I just needed to get better at my job.”
Haley also has a child with disabilities which means leaving early or staying home more than a typical parent would. She was promised flexibility, but after a while she said her her inability to be there every day was “ruining her reputation and people couldn’t rely on her.”
“I was crushed.” she said. “It felt like everything I’d worked for in my career was dismissed in a single sentence.”
In the end, she was let go under an assumption that wasn’t true. Her boss even told her, “I don’t even need to hear the whole story.” This was after almost 2 years of her time.
Haley told me, “Hind sight’s 20/20. I should’ve noticed it so much earlier. The turnover was really high; he actually let someone go just 3 days after being hired. He kept toxic employees that did everything he asked but who slowly ruined the team when he was gone. And the hardworking people, he always ended up letting them go.”
There were free snacks in the kitchen. A gym in the building. Annual team retreats. Monthly town halls. All of it looked right. It wasn’t. not even close.
She said, “It was one of the most elaborate fake cultures I’ve ever encountered.”
After our conversation, it made me think about how often founders talk to me about their own company’s culture. They either want to make sure they create a good one or need help figuring out how to fix it.
Here’s the thing you want:
You want to build something people are genuinely proud to be part of, where nobody’s updating their LinkedIn on a Tuesday afternoon because they’re miserable.
Most founders want that. The problem is the ones who don’t have it usually think they do, and the gap between what they say their culture is and what people actually experience is where their company quietly fall apart. High turnover, disengaged teams, people doing the bare minimum, good people leaving for no obvious reason — that’s not a hiring problem or a compensation problem, that’s a culture problem.
“ Corporate culture is the only sustainable competitive advantage that is completely within the control of the entrepreneur.” — David Cummings, Co-founder of Pardot
Here’s how to do it:
Define your culture by what you do, not what you say. You can put your values on the wall. You can send the all-hands email. You can have 1:1s and coach people. None of it matters if your highest performer treats people like crap yet you keep promoting them. When you do that, what you’re actually telling your team is values are decorative and performance is the only currency that matters.
When a founder says they care about work-life balance and then sends a Slack message at 11pm and expects a response or says they value transparency and then makes major decisions without explanation, people lose faith. It only takes a few inconsistencies before the trust is gone, and once it’s gone you’re not getting it back by throwing a company retreat at it.
Be 100% honest about what the job actually is before someone takes it. Not the aspirational version, the realistic version, including the parts that aren’t great. When you don’t clearly define the role or expectations, you’re not just disappointing people, you’ve made them feel lied to. People can handle hard things. They usually don’t tolerate handle being misled.
Don’t tolerate poor behavior. Fire someone for violating company values the same way you’d fire for under-performance. Most founders never do this because a violation of cultural expectations can be really hard to quantify. They’ll let someone go for missing targets but keep someone who’s making people miserable.
We all know when you have to let someone go who is genuinely great at their job, it’s easy to hesitate. They can do things nobody else on the team can do, they’re fast, clients love the output, and losing them feels like a real business risk. But they’re dismissive of people who disagree with them, they cut corners on the work that isn’t exciting, and the people around them start to either retreat or leave. Maybe you think the output justifies the behavior. It doesn’t.
Cutting toxic employees, regardless of their skills is always the right move. — Gary Vaynerchuk
Listen and pay attention to the culture people are experiencing. You can usually tell you have a bad culture even if you don’t want to admit it. Yea, the gym and the snacks and the team trip, those things are great, but it’s just marketing; it’s what the culture looks like from the outside. What it should feel like on the inside is that managers actually have their team’s back when things go sideways and people are trusted to do the job their job with being micromanaged. But if you actually listen to people in your 1:1s and they’re telling you differently, you need to address it immediately.
The uncomfortable truth. Many founders don’t understand that people who work the hardest aren’t the ones you pressure into it, they’re the ones that do it because that’s who they are. Those are the people you want on your team, but they’ll only stay as long as they feel trusted, supported, and not taken advantage of. Their work may be slow at times, but unfortunately, most founders don’t have the patience for slow when they’re trying to grow fast.
And you can’t measure commitment to the company by how much you’re willing to sacrifice for it, and then use that as the standard for everyone else. That’s the thing founders miss most often: your tolerance for the grind is not a baseline. It’s just yours. Expecting your team to care as much about the company as you do is a losing strategy. The company is your baby, the weight of success or failure is ultimately on you. Not them. So don’t expect them to act like it is. Respect their boundaries, and then success is far more likely.
One more thing worth saying: the culture you build in the first ten people is almost impossible to change at fifty. Not because people resist change, but because culture is self-selecting. The early team attracts the next wave, and if they’re burned out, cynical, and keeping their heads down, that’s what you’re recruiting into. I’ve seen founders try to fix culture at scale and it’s brutal, not impossible but brutal, because you’re essentially asking people to unlearn the survival behaviors they developed working for you.
The time to get this right is before you think you need to.
Now go:
This week, try this:
If you haven’t specifically thought about what culture you want for your company, start there first. Write a few things down about how you want your company to feel to others. If you already think you know that, think about one person on your team who is high output but low culture fit. Not someone you’d call a bad person, just someone whose behavior, if everyone on the team behaved the same way, would make the company worse. Write down what you’re tolerating and why. Then ask yourself if you’d hire someone today knowing they’d behave exactly that way. If the answer is no, you already know what to do.
Start here if you only have 10 minutes:
Ask one person on your team, someone who isn’t a direct report and who you know will tell you the truth. Ask them how they’d describe the culture to a friend who was thinking about joining. Don’t prompt them, don’t lead them. Just listen. What they say will tell you more than any engagement survey.
Next Tuesday: The Genius Guide on When to Pivot and When to Move on
P.S. The hardest part of building a real culture isn’t making sure you’re providing all the bells and whistles, it’s being honest about any gap between what you say and what people are actually experiencing. Several founders I know have had moments where someone on the team finally told them the truth and realized they’d been the problem the whole time. That’s uncomfortable. It’s also the only way you actually fix it.
If this resonated, hit reply and tell me what your culture looks like on paper versus what it looks like in practice. I read every response.
Writing from Austin, still learning and listening,
Alex
We also work with founders and teams on ghostwriting and go-to-market support—helping turn ideas into clear content for positioning, launches, and distribution.
If that’s something you’re thinking about, happy to chat. Feel free to put some time on my calendar here.
The worst is when founders and entrepreneurs justify their expectations by saying “we’re a startup, this is normal around here” or “you’re expected to wear many hats.” 🙄 thanks for sharing this piece! It brought back a lot of trauma of when I used to work for startups! 😅