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

How do AI tools decide which brands to recommend?

AI tools tend to recommend the brands that are linked to and mentioned on pages closely related to their industry. In research shared by Ben Wills of OppAlerts in October 2026, covering 100 industries, 16 AI models, ChatGPT and Google AI Overviews, that pattern showed up more than 20,000 times, and it held for brand mentions without a link too.

Answered Oct 12, 2026 · Founders and marketers who want ChatGPT, Google AI Overviews and other AI tools to mention them

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

What is my company worth?

Your company is worth a range, not a number. Where you land in that range comes down to three things: how predictable the revenue is, how concentrated your customers are, and how much the business depends on you. Retention moves your value more than anything else.

Answered Oct 5, 2026 · Founders who've had a buyer call, or expect one in the next few years

How much will I actually take home when I sell my company?

Less than the sale price, often a lot less. Debt and deal costs are paid first, then investors' liquidation preferences, then everyone else by ownership, and then taxes. Compare offers on cash at close, not the headline price.

Answered Oct 5, 2026 · Founders comparing offers, or wondering what an exit would really mean

How do I know if my startup idea is any good?

Ask five people who have the problem to pay for it. A good idea solves a frequent pain that someone already spends money on, for a buyer you can name and reach cheaply, with a reason it should be you. You can test all of that in two weeks.

Answered Oct 5, 2026 · Founders before they quit their job, or before they spend six months building

Who is my ideal customer?

Your ideal customer is defined by the problem, not demographics: a type of company with an urgent trigger, a person who owns the problem and can sign, a pain that costs them money, time or risk, and a place they already gather. If you can't turn it into a list of 100 names, it isn't specific enough.

Answered Oct 5, 2026 · Founders selling to everyone and closing too few of them

Should I start a company or stay employed?

Start a company only if you can live with years of uncertainty, you have a specific problem pulling you rather than a wish to be your own boss, and you're ready to own everything. If one of those is missing, a great job building inside someone else's company is the better bet.

Answered Oct 5, 2026 · People with a steady job and an idea they can't stop thinking about

What's capping my company's growth?

Usually one constraint, and it's often the founder. Most stalled companies have a single bottleneck, such as decisions that all route through one person, a sales process only the founder can run, or a structure nobody has rebuilt since the company was ten people. Fix that one and the rest moves.

Answered Oct 5, 2026 · Founders whose company has stalled even though everyone is working harder

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