The big decisions founders face, and what I'd do.

Should I raise money, or stay bootstrapped?

Raise only if you are capital-constrained — you know exactly what repeats, and the only thing between you and more of it is money. If you are still learning which customers stay and why, a round buys eighteen months of not knowing with a board watching. Most companies between $1M and $10M in revenue are evidence-constrained and think they are capital-constrained.

Answered Aug 14, 2026 · Founders assuming they have to raise, and founders going slow when they shouldn't

What should I charge, and how do I raise prices without losing customers?

Price against the line item you replace in your customer's budget, not against what it costs you to deliver. Raise it on new customers first — nothing breaks, and within a month you have evidence instead of a theory. Then move the existing base in tiers, smallest accounts first, with ninety days' notice and one honest paragraph.

Answered Aug 18, 2026 · Founders with real revenue and a price they set years ago

How do I stop being the bottleneck in my own company?

Log two weeks of your real time, name one owner per function, give each owner one number, and write down the dollar threshold above which a decision comes to you. Then leave for two weeks without checking in. Whatever breaks while you're gone is the actual list — everything else was a guess.

Answered Aug 21, 2026 · Founders between $1M and $10M who are in the middle of every decision

How do I sell when I'm the only one who can close?

Write down your last twenty deals, won and lost — the pattern in that list is already your sales process, you just haven't documented it. Record yourself selling, build the script from your own words, then hire one seller and give them the small deals while you keep the top of the market. When their numbers approach yours, the motion is real.

Answered Aug 25, 2026 · Founders who are still the only one who can close

Who do I actually need to hire in the AI era?

Hire judgment, not help. Help does tasks you define, and that's the part that got cheap; judgment decides what should be done at all, and that hasn't moved. Write the role for the team you'll have in eighteen months — for most functions that's one strong leader plus tooling, not a leader plus five juniors.

Answered Aug 27, 2026 · Founders building a team that will be smaller and denser than the last one

What should I actually be doing with AI this quarter?

First decide whether AI changes your product or just how you run — most founders confuse the two and panic about the wrong one. If the customer's job now gets done a new way, that's urgent and it's a product question. If not, pick two workflows, make them boring, and keep a human at the last mile of anything a customer sees.

Answered Sep 2, 2026 · Founders who feel behind and aren't sure what they're behind on

What do I need to know before my first board meeting?

Send the material 48 hours ahead with the bad news first, then spend the meeting on the two decisions you actually need rather than reading slides aloud. Build the board on purpose — two founders, one investor, one independent who has actually run something — and read your protective provisions once, slowly, before you ever need them.

Answered Sep 4, 2026 · First-time founders raising, or sitting in front of a board for the first time

How do I value a private company doing $1M to $10M in revenue?

Most private companies at this size are valued on a multiple of revenue or of owner earnings, and the multiple is set by three things: how predictable the revenue is, how concentra…

Answered Sep 8, 2026 · Founders between $1M and $10M who want a real number, not a fantasy

Should I move off per-seat pricing, and how do I reprice without losing customers?

Move off per-seat pricing when your best customers get more value while using fewer seats — that is the moment the seat stops tracking value and starts working against you. Do not …

Answered Sep 10, 2026 · Founders with real revenue and a price they set years ago

How do I tell if I'm the bottleneck in my own company, and how do I get out of the way?

You are the bottleneck if work waits on you. The test is not how busy you are — it is how long things sit. Track how many decisions in a week route through you and how long each on…

Answered Sep 11, 2026 · Founders between $1M and $10M who are in the middle of every decision