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Unpopular opinion: Free mentorship is quietly killing startups.

  • 2 hours ago
  • 4 min read

After 500+ mentees, I can tell you with certainty — the founders who succeeded, raised the capital they needed, and actually did the work were the ones with financial skin in the game.


Every. Single. Time.


And I know what you’re thinking. “But mentorship should be accessible. Knowledge should be shared freely. Pay it forward.”


I’ve heard it all. I believed it once too.


But here’s what 500+ relationships taught me that no business school will:

Commitment without cost is just a conversation.

The data doesn’t lie. A Harvard Business School study found that individuals who financially invest in coaching and advisory services are 4x more likely to implement the guidance they receive. Not because the advice is better — but because they showed up differently from day one. Money reframes the relationship from casual to contractual. From “nice to have” to “I need to execute on this.”


The Founder Institute tracked advisory relationships across hundreds of startups and found that 57% of advisors deliver fewer than 5 meaningful hours per year once the agreement is signed. Equity alone doesn’t create urgency. It creates entitlement on both sides — the founder expects magic, the advisor expects passive upside. Nobody does the real work.

That’s not a partnership. That’s a polite transaction dressed up as mentorship.


And on the mentor side? The “old way” says you build an advisory board, you give generously of your time, your network, your hard-won knowledge — and you do it largely for free or for a fraction of a percent of equity that may never be worth anything. You bleed. They grow. Maybe.


I’ve sat across from brilliant founders who nodded at everything I said and implemented nothing. No urgency. No follow-through. No stakes.


And I’ve sat across from founders who invested real dollars in the relationship — and watched them move mountains between sessions because they couldn’t afford not to.


Now let me say something that’s going to make some people deeply uncomfortable.


I run a diverse, women-owned business. I didn’t choose that label — it gets applied to me constantly, along with all the pressure and expectation that comes with it. The unspoken rule seems to be that I owe my community something. That I’m supposed to pour myself out for free because of what I represent.

Here’s my honest experience:


Almost every female or BIPOC mentor I sought out early in my journey was unavailable, gatekeeping, or — and I’ll never forget this — literally told me “it was hard for me and I’m not sharing.”


Let that land for a second.


So you know who actually mentored me? Who opened doors, made calls, sat across from me and treated my business like it deserved to win?


Middle-aged white men.


I’ll wait.


They didn’t care about the labels. They didn’t see a “diverse founder” who needed a photo op or a checkbox. They saw a builder who was serious, and they got to work. They poured into me without an agenda. They made introductions that changed the trajectory of my company. And I am genuinely, deeply grateful to them — because they showed me what real mentorship looks like when it’s stripped of politics and performance.


It was never about identity. It was about execution.

And that experience fundamentally shaped how I show up as an advisor today — and why I refuse to mentor for free out of some sense of cultural obligation. Because obligation-based mentorship helps no one. It breeds resentment on one side and entitlement on the other.


So what actually works?

The hybrid model.

Equity AND cash. Together.


This is where the magic happens — and frankly, it’s where the industry is heading for a reason. When a founder pays a monthly retainer or project fee AND grants a small equity stake, something fundamentally shifts in the dynamic.


The cash creates immediate commitment. It signals that the founder is serious, resourced enough to invest, and expects results — not just coffee chats and encouragement. It also compensates the advisor fairly for their time in the present, not in some hypothetical future exit.


The equity creates long-term alignment. The advisor is now a stakeholder. They’re not just dispensing wisdom and moving on — they’re rowing the same boat. They make introductions that matter. They lose sleep over your problems. They show up differently because the outcome affects them too.


Cash without equity = a vendor relationship. Transactional. Finite.


Equity without cash = an unbalanced bet. Undervalued on both sides.


Cash AND equity = a real partnership with teeth.

Founders who structure engagements this way report faster fundraising timelines, stronger investor networks activated on their behalf, and advisors who are genuinely reachable when a crisis hits at 11pm before a term sheet conversation.


The best mentors in the world don’t work for free. And if they do, you probably aren’t their priority.


That’s not cynicism. That’s economics. Attention flows where incentive is.


If you’re a founder still trying to cobble together a free advisory board because that’s what the playbook said to do — I’d challenge you to rethink it. One committed, compensated advisor who is financially aligned with your outcome will outperform five free ones every time.


And if you’re a mentor or advisor still bleeding your time and energy into relationships that cost the other party nothing — ask yourself honestly: are they actually doing the work?


Or are they just showing up for the free advice?

Skin in the game changes everything. The labels don’t.


Drop a comment if you’ve lived this — as a founder, a mentor, or someone who’s been on the wrong end of performative support. This conversation is overdue.



 
 
 

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Maresa Friedman is The Executive Cat Herder—known for bringing order to chaos, clarity to strategy, and leadership to rooms where everyone’s talking but no one’s aligned. With a background in scaling companies and advising founders, she wrangles complexity with precision and turns big vision into executable moves.

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