Ask the Expert: Culture in your Company
Ask the Expert: Culture in your Company
Register for Elevate CEO Retreat, Oct. 27-30
I’ve built two companies repeatedly recognized as “Best Places to Work” in the Washington DC area, and they weren’t fluff-and-perks companies. At TRS and Sequoia Holdings, I scaled high-performance cultures inside defense contracting and software engineering (industries not exactly known for warm-and-fuzzy vibes). Let me tell you what no one told me: When you only have 2-10 employees, every hire changes your company’s DNA. Get it right, and you create a force multiplier. Get it wrong, and you spend months fighting fires, replacing people, and watching morale slip. Between $250K and $3M, your growth depends less on you doing more… and more on whether you can attract and keep the right people. Quick Note: Final two spots remaining for my Elevate CEO Retreat, October 27-30, Surf City, North Carolina. If you're an early-stage founder in the weeds making your first few hires, we'll fix these problems together with 10 other founders at your exact stage. At its core, culture is “how we do things around here.” The unwritten rules that determine:
The main mistake founders make is thinking they’ll “figure it out later” after they’ve nailed product-market fit. But by then, you’ve already installed defaults that are 10x harder to fix. Why Culture Breaks at the Early StageI’ve watched dozens of promising startups hit the same wall. Founders hire fast to relieve pain, but without defining what “good” looks like. They over-index on technical skill, under-index on behaviors, and fail to set clear expectations. The result? Culture debt - misaligned hires, turnover, and a team that feels like strangers rather than co-owners. Here’s what it actually looks like:
By the time you’re at 20 people, you’re spending half your time untangling confusion rather than driving growth. The Cost of Getting This WrongWhen culture rots, four things happen: 1) Top performers leave Your highest-output engineer resigns after six months because they’re tired of shipping great work only to see decisions reversed in private Slack threads. Big financial cost to replace, plus months of lost velocity. 2) Execution drags Projects take 2-3× longer than planned because nobody knows who owns what. Two people work on the same feature, or nobody touches it because “I thought you had it.” You miss product deadlines, burn investor trust, and ship late fixes. 3) You become the bottleneck Every question, from pricing tweaks to vendor choices, lands in your inbox. Your Slack DMs fill with “Hey, quick question…” You haven’t had a deep-work block in days. Growth stalls not because of product but because the org can’t move without you. 4) Hiring gets harder Your company earns a reputation for chaos. Candidates start asking, “How many hours do people really work?” or “Why did your last head of product leave?” You pay 15-20% higher salaries just to convince people to join. Five Steps That Actually WorkHere’s what worked at both my companies: 1. Turn Vague Values into Real Behaviors“We value ownership” means nothing. “We flag blockers early and ship even when it’s imperfect” does. Rewrite your values as testable behaviors:
2. Filter for Behavior Before You HireCreate a scorecard for every role with 3-5 non-negotiable behaviors. Then design interviews around them: “Tell me about a time you disagreed with a founder or lead, what happened?” “What’s a mistake you made that no one noticed?” Reference check like an owner: “When did you trust them least, and what did they do next?” If someone makes you nervous now, they’ll cost you 3+ months of cleanup later. 3. Standardize The First 90 DaysCreate one onboarding doc with:
Book these in advance:
4. Run Weekly and Monthly Operating CadenceInstall three simple rituals: Weekly standup Covers only: metrics → priorities → blockers → wins Done async with a remote team? Use Loom with same structure Monthly retro “What’s working?” “What’s confusing?” “What needs to change?” Decision log
If you don’t write it down, you’ll re-debate it three months later. 5. Delegate Culture Ownership Before You Need ToPick 1-2 team members who model your behaviors. Give them authority over onboarding, retros, and feedback loops. If the team pauses every time you’re not in the room, you’ve built dependence, not alignment. The Compounding Value of Getting It RightWhen you nail these fundamentals:
Both TRS and Sequoia grew for 7+ years straight, with single-digit turnover, while maintaining the culture we built early. Because we had systems that reinforced the behaviors we valued. This is why Drucker’s “culture eats strategy for breakfast” has such truth to it. A brilliant roadmap without cultural alignment is like building on swampland. Looks solid at first, then starts sinking under its own weight. This erosion is a silent killer: mis-hires you didn’t course correct, values you didn’t enforce, confusion you let slide because you were tired. And trust me on this: early culture is easier to shape than to fix. If you’re at $250K-3M ARR and feel like the bottleneck, now’s the time to fix this. We’ve got two seats left for October’s Elevate CEO retreat, specifically for founders hitting this growth stage. Build the company your team wants to stay at, and your future self won’t have to fix. October 27-30Surf City, North Carolina |
“We value transparency”
“We document every decision over $1K and link it in Slack within 24 hours.”
“We move fast”
“We ship something live every week. We push work-in-progress code to GitHub every 48 hours, even if it’s not finished.”
“We’re customer obsessed”
“We tag every support conversation with at least one insight and review top 3 themes each Friday.”