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How mentors can find founders worth helping

Your time as a mentor is limited. What to look for in founders, how to filter by what they've shipped, and how to mentor without burning out.

Guru Raj Kolipakula5 min read

Most advice about mentoring is written for the person who wants a mentor. Very little is written for the mentor: the operator, engineer, investor or former founder who'd genuinely like to help, and keeps getting vague "can I pick your brain?" messages from people they know nothing about.

The problem isn't a shortage of founders. It's telling, quickly, which founders will actually do something with your time. Here's a practical way to find them, and to keep mentoring from quietly eating your week.

Start with what you're actually good for

"Happy to help founders" is too broad. Nobody knows what to ask you, so they ask everything. Narrow it to two or three things you've done yourself:

  • Pricing a B2B product for the first time
  • Hiring the first three engineers
  • Running a seed round
  • Getting a hardware prototype made
  • Selling to hospitals, schools or city governments

Say it somewhere people can see it. The founders who need exactly that will find you, and the rest will self-select out. That saves both sides a meeting.

Decide on a cap before you start

When someone offered free mentoring on Hacker News in 2021, the replies came fast. Within a few comments they wrote that they'd "probably cap it at 10 people." That's a healthy instinct. Without a limit, mentoring turns into a second job, and the quality drops for everyone.

Pick a number you can sustain, say three to five founders at a time, plus a fixed slot for one-off questions. When the slots are full, say so.

Know what you're looking for

Paul Graham's "What We Look for in Founders" lists determination first and says it "has turned out to be the most important quality in startup founders," ahead of raw intelligence. In his essay on angel investing he gets closer still: the opposite of a hapless founder is one who is "relentlessly resourceful."

That's useful for mentors too, because resourceful founders are the ones who turn advice into action. You can't see determination in a pitch, but you can see its traces:

  • They've shipped something. A launched product, a prototype in users' hands, a first sale. Even small, finished things count.
  • They come with a specific question. "Should we charge per seat or per location?" beats "what should we do about pricing?"
  • They've already tried something. They tell you what they did and what happened, not just what they're planning.
  • They come back. After you suggest something, they return with the result, good or bad.

A commenter in a 2022 HN thread on finding mentors described the mentor's side of this well. Experienced people "usually like to spend any amount of time explaining, if they see that you're someone who might be able to understand the answer." Effort and follow-through are what make a mentor want to keep going.

Filter on output, not on the pitch

The founders best at pitching aren't always the ones best at building. A few quick filters:

  1. Ask what they shipped in the last month. Not the roadmap. What's live now?
  2. Look at the trail. Changelogs, release notes, launch posts, a public repo. A steady record of small releases says more than one big announcement.
  3. Ask for the number they watch. Founders who know their one number, whether that's weekly users, revenue or retention, are usually paying attention to the right things.
  4. Check the stage fit. Your advice is most useful to people one or two steps behind where you've been. If you've scaled a sales team, a founder still looking for a first customer may need someone else.

Give one piece of advice, then watch

The simplest test is also the fairest. In the first conversation, give one concrete suggestion, the smallest useful thing they could do this week. Then wait.

Founders who come back having tried it, even if it failed, are the ones worth more of your time. Founders who come back with a new set of questions and nothing tried usually aren't ready for a mentor yet. That isn't a judgement of them as people. It's a signal about timing.

Meet in person when you can

A thirty-minute coffee or an hour of co-working in the same café tells you more than a dozen messages. You see how someone thinks out loud, how they react to pushback, and whether they're actually building while you sit there.

Keep it simple and public: a café, a library, a coworking space. Hold the same slot each week or month so founders know when to find you, like open office hours.

Track the trajectory, not the conversation

After a month, ask yourself one question about each founder: did they move? Shipped the feature, ran the experiment, made the call they were avoiding. Those are the people to double down on. It's also how you'll know your time is doing something.

Say no clearly and kindly

You'll turn down more people than you help. A short, honest reply is better than silence: "I'm full right now. You'd get more from someone who's done X. Try again in three months with what you've shipped since." Plenty of founders will take you up on that, and they'll come back stronger.

Where The Build Nation fits

The Build Nation is a free, real-time network for builders, investors, mentors and businesses, live in San Francisco. It's built around output, which is exactly the signal mentors need.

Every member profile shows what someone has done rather than how popular they are: things they've shipped, launches, and an 18-week proof-of-work grid built from launches, "Shipped:" updates and meetups where both people confirmed they met. Likes and follower counts never count. You can read exactly what goes into it on how ranking works.

You can set "Here to" on your profile to mentoring others, so founders know what you're offering. In Meet, the people suggested to you are ordered by field and stage, and you can filter by stage to find founders at the point where your experience applies. To run office hours, start a quick meetup at a café, add a question for people to answer when they ask to join ("What are you stuck on this week?"), and review each request before accepting. Accepted people get a chat with you so you can sort out the details.

Mentoring isn't a separate mode in the app, and there's no paid matching. It's the same tools everyone uses, pointed at the people most likely to do something with your help.

Sources

  1. What We Look for in Founders (opens in a new tab) · Paul Graham
  2. How to Be an Angel Investor (opens in a new tab) · Paul Graham
  3. Ask HN: How to find mentors? (opens in a new tab) · Hacker News
  4. Ask HN: Do any beginner coders or those interested in tech want a free mentor? (opens in a new tab) · Hacker News
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