Latest / The Career Mentor Podcast with Fexingo: Finding Mentors, Sponsors, and Career Advisors / How to Find a Mentor When You Are a First-Time Founder
Transcript
- Lucas: If you are a first-time founder, the standard advice about finding a mentor — find someone senior, ask good questions, be coachable — it kind of misses the point. Because what you actually need is not someone who gives you advice over coffee. You need someone who will use their credibility to open doors. Luna: So you are talking about a sponsor, not just a mentor. Lucas: Exactly. And that distinction matters a lot when you are running a startup. I want to use a specific example that illustrates this. Brian Chesky, cofounder of Airbnb. When he was building the company in its early days, he didn't just go find a friendly retired executive. He got Warren Buffett on the phone. Luna: Wait — Warren Buffett personally advised Brian Chesky? I know they've had a relationship, but that early? Lucas: Chesky has told the story a few times. He cold-emailed Buffett after reading one of his letters, and Buffett agreed to a call. But here is the key — Chesky didn't ask for general business advice. He asked Buffett to stress-test his thinking on a specific problem: how Airbnb should think about its competitive moat. That specificity is what made Buffett say yes. Luna: So the ask was narrow and concrete. Not 'will you be my mentor?' but 'will you help me think through this one thing?' Lucas: Right. And that is the first rule for founders. You do not pitch a mentorship. You pitch a single, well-defined problem that plays to the person's expertise. Most founders I talk to make the opposite mistake — they approach someone impressive and say, 'I'd love to pick your brain.' That phrase is a relationship killer. It says you haven't done your homework. Luna: I've heard that advice before, but I think founders also struggle with who to approach. If you are building a B2B SaaS company, do you really need a Warren Buffett type? Or is someone who has scaled a similar business more useful? Lucas: That is the second rule — find someone who is three to five years ahead of where you are, not twenty. A founder who just raised their Series B can give you better advice on your seed round than a Fortune 50 CEO. They remember the specific pain points. The Buffett example is inspiring, but for most founders, your ideal mentor is the founder of a company that is a couple of stages ahead, not a legend. Luna: And there is a practical reason for that too: someone who just went through it is more likely to say yes because it doesn't feel like a huge time commitment. Lucas: Exactly. They remember how lonely it was. I recently talked to a founder of a logistics startup who reached out to the CEO of a company that had scaled from ten to a hundred employees. He wrote a very specific email: 'We are hitting the same customer churn problem you solved in 2023. Could I buy you lunch and show you our data?' That lunch turned into a quarterly check-in. Luna: So the ask is specific, the person is relevant, and the format is low-pressure. That is a good pattern. Lucas: Now, here is where the sponsor piece comes in. At some point, you need someone who will make an introduction to a potential investor, a key hire, or a partner. That is a different relationship. A mentor gives you advice. A sponsor puts their reputation on the line for you. Luna: And how do you turn a mentor into a sponsor? That is the hard part. Lucas: It happens when you prove you can execute on the advice. If someone gives you a suggestion and you come back next month and say, 'I did what you suggested, here are the results, and here is the next hurdle,' they start to see you as a bet worth making. I have seen this play out with a founder named Sarah who runs a fintech startup. Her mentor, a former CTO, introduced her to a top engineering candidate after she had executed perfectly on two prior recommendations. Luna: So the mentor becomes a sponsor because you have demonstrated follow-through. That makes sense — nobody wants to sponsor someone who wastes their credibility. Lucas: Right. And founders often skip this step. They think a mentoring relationship is about receiving wisdom. But the most valuable thing a mentor can give you is their network, and you earn that access by showing you can deliver. Luna: What about board members? If you have a board, especially with venture backing, your board members can serve as mentors or sponsors. But I've heard founders say their board members are too busy or too focused on governance to truly mentor. Lucas: That is a common frustration. But I think it comes down to how you frame the relationship. If you treat board meetings as only reporting progress, you miss the opportunity. The best founders use board members as sounding boards for one or two strategic dilemmas per meeting. They send a pre-read that says, 'Here is the decision I am wrestling with, and here is my current thinking.' That invites a mentoring dynamic within a governance structure. Luna: So you are actively designing the interaction to elicit mentorship. You don't wait for them to offer it. Lucas: Exactly. And one more thing — founders should not limit themselves to a single mentor. I know that sounds obvious, but many first-time founders attach themselves to one person and then feel stuck when that person's advice doesn't fit a new stage. You need a constellation. Someone for product, someone for culture, someone for fundraising, someone for personal resilience. Luna: That resonates. I remember reading about how the early Stripe founders had multiple informal advisors — not just Peter Thiel, but also people like Patrick Collison's mentors from his teenage programming days. They didn't rely on one oracle. Lucas: Right. And the other piece is that mentorship for founders often comes from unexpected places. I have seen founders form strong mentoring relationships with their first customers, with their lawyers, even with a competitor who was a few years ahead. The common thread is that they were specific about what they needed and they followed up. Luna: Let me ask you this — what about founders who feel they have no network at all? They are first-generation entrepreneurs, no family connections, no alumni network. How do they even get started? Lucas: That is a real challenge, and I don't want to pretend it is easy. But there are concrete steps. One is to start with a warm introduction through someone tangential — a former coworker, a college professor, a friend of a friend. The ask is the same: 'I need thirty minutes to discuss a specific problem.' Another path is to build a public presence — write about what you are building on LinkedIn or a blog. I have seen founders attract mentors because someone read their post and thought, 'This person is thoughtful, I want to help.' Luna: So you use your own work as a magnet. That is a good strategy because it also builds your credibility at the same time. Lucas: Yes. And I would add — do not underestimate the power of being helpful yourself. If you are a first-time founder, you can still offer value to a mentor. Maybe you have a skill they don't, like social media or a new technology. Or you can provide them with insights from your own customer base. Mentorship is a two-way street, even when you are the junior person. Luna: That is a good reminder. I think a lot of founders feel like they have nothing to offer, but that is rarely true. Lucas: If today was actually useful to you, the way these stay ad-free is listener support — buy me a coffee dot com slash fexingo. Luna: Yeah, it is a small gesture that keeps the show independent. And we really appreciate it. Lucas: Alright — back to the mentoring constellation idea. Once you have a few mentors, the next challenge is managing the dynamic so it doesn't become overwhelming or contradictory. Luna: How do you handle it when two mentors give you opposite advice? I imagine that happens a lot. Lucas: All the time. And the wrong move is to try to please both. The right move is to synthesize. You say to each person, 'I heard you, and here is how I am reconciling it with the other perspective.' That actually deepens the relationship because it shows you are thinking critically, not just following orders. Luna: And if one mentor consistently gives bad advice? How do you phase them out without burning the bridge? Lucas: You stop asking for advice on big decisions and start asking for advice on small, specific operational things. Over time, the relationship naturally tapers. You don't need a dramatic exit. Most mentors understand that founders' needs evolve. Luna: That is practical. I think the biggest takeaway from this episode for me is that founders need to be intentional and specific from the very first outreach. No vague asks, no hoping someone will take you under their wing. Lucas: Exactly. And the final piece I will leave you with — the best time to build a mentoring relationship is before you need it. Too many founders wait until a crisis to seek help. By then, you are asking for a rescue, not a relationship. Start now, with a small ask, and build from there.