One Simple Lesson That Made Me A Better Investor & Mentor

I used to give advice to people all the time. I wanted to be helpful. But really, I was just annoying.

When Zak Holdsworth and I met, he told me about his vision to help scalehigh-quality affordable healthcare. His company Hint Health is building a streamlined back-end for healthcare systems which makes care more affordable. Zak’s idea is undoubtedly going to revolutionize the industry. As an investor, I was excited to share my thoughts on what he should do. But here’s the thing: I waited for him to ask for help.

The number one question I get from investors is, “How do you control the outcome?” We’re all grasping at straws to feel more secure, confident, or in control of our investments. But the only control I need is moral persuasion. If someone believes you enough, they’ll listen to you. I believe that Zak is a great leader. He is charismatic and entrepreneurially smart: he can draw people in as allies, and believes in investing in people just as I do. He told me he wanted to close more deals and learn how to scale.

I focused on setting up a strategy, and clarifying the tactics needed to get there. Zak said, “You helped me think about building a scalable sales process from day one, and to become metrics-driven early so when we start to scale, we don’t need to backfill.”

I helped Zak identify Hint Health’s target market of membership-based providers and find the fastest path to growth. In his case, this was hiring an experienced sales professional. Since then, Zak’s made the hire and business is going great. “You’ve helped me be a better leader,” Zak told me. And the feeling is mutual. Zak knows when to ask for help, so our relationship is about collaboration rather than tutoring. We’ve invested in each other and built mutual trust.

What I’m saying is, only help when you’re needed…get out of your own way when you’re not. One of the best things that’s happened to me is that I stopped going out of my way to give advice. If someone asks, I’ll help; if they don’t ask, it’s not my place. Since that realization, my life has gotten a lot easier, (and everyone else is a lot less irritated). That’s how Zak and I have effectively collaborated…and the advice he used to grow the business.

Blake West

Cofounder, CTO at Warbler Labs, supporting Goldfinch (We're hiring!)

8y

Hey WIll, I'm an engineer at Hint Health, and was the first hire. I work with Zak Holdsworth every day. One of his strengths is unabashedly asking for feedback and insights on virtually everything he does. So that fits well the rule you espouse in this post. But for your other mentees who aren't so forward, do you let them know up front about this rule? Or do you only invest in more "forward" types? :)

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Dustie Zvolanek

Real Estate Expert & Mentor. Investment Home Specialist. Creative Thinker. Problem Solver.

8y

Great article and advice!

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Baker Humadi

Software Engineering Manager at NVIDIA

8y

Great article. I don't think many people get of their way to help. It is very nice to know such people exist.

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Zach Warder-Gabaldon

Accelerating New Zealand's economic growth through innovation | 20 years, 8 startups, 2 exits, and an abundance of failures, successes, and learnings in Silicon Valley

8y

Love the clarification on collaboration between investors and entrepreneurs rather than an oft-perceived unilateral relationship, Will.

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