Coached Every Step of the Way - An Interview with iiED Mentor Brooks McChesney
Picture a startup founder and you’ll see someone brimming with passion, energy and stamina. But without prior connections or experience, getting from pitch to product, building trust with investors, and growing a company can be a struggle. That’s where having a great mentor comes in. By bringing experience, connection, and credibility to a startup, mentors can help entrepreneurs gain investors, focus their ideas, and grow as a business.
Take Brooks McChesney, Silicon Valley veteran, mentor and Advisory Council Member at CSUMB Institute for Innovation & Economic Development (iiED). The Silicon Valley veteran has mentored and coached a multitude of startups from pitch to acquisition and beyond, including recently acquired dermatology telemedicine startup— and 2012 Startup Challenge Venture Division Winner— Apostrophe (formerly YoDerm).
But what makes a great mentor? And how can mentees make the most of their experience? I sat down with McChesney to learn more about mentorship, coachability, and how iiED creates startups worth investing in.
How did you become involved with iiED?
Well, it goes back several years. I had been involved with several business incubators. I’m a 30 year Silicon Valley veteran. I had been on the boards of the NASA Ames Business Cluster and the San Jose Business Cluster, two leading incubators in Silicon Valley. When I came down here, I found out about the Marina Tech Cluster, and I thought it might be fun to get involved.
I got involved at the very beginning of the Startup Challenge. When it got switched over to CSUMB, I stayed, and have been involved ever since. Today, I spend half my time coaching for-profit companies and half my time doing the same thing, volunteering with non-profit companies in the greater Monterey area through the Community Foundation. This is one of the things I love to do and it’s a way to give back and help people.
Could you describe your role as a mentor?
When I was an entrepreneur, I had categories of mentors that I was looking for. There were people who brought a lot of credibility to the company just by being affiliated with them. The second category is specialists in a particular area, who could be door openers, make critical introductions and bring their network to the company. The third level, where I typically play, is more of a strategic advisor who gets involved in day-to-day activities, either as a mentor or, in some cases, a board member, depending upon what the company wants.
I typically start by getting to know them for a period of a few weeks to over a month, trying to understand their business and see if there’s a way that I can help them. It’s all about building confidence and trust. I find that one of the things that the mentor can do very successfully is be the trusted advisor who can answer questions that the entrepreneur may not want to raise with his/her board, and help them solve particular problems before they escalate to the board level.
Part of what I try to do is anticipate potential issues so there are no surprises and no hiccups. Typically, the early and young entrepreneur is full of passion and enthusiasm. I help channel the enthusiasm that I see in the entrepreneur, by helping develop a greater sense of focus and prioritization
How can entrepreneurs maximize their mentorship experience? What makes some people easier to coach than others?
The first instinct of an entrepreneur is to be a little bit suspicious when somebody comes in and says, “I can help you.” Once an entrepreneur starts to get visibility, everybody wants to get involved with a perceived winner. Too many coaches can kill the golden goose and some are not as good as others.
The first critical thing is building that sense of trust. I was a mentor for YoDerm (now Apostrophe) from start to exit, and began working with them when there were just the two founders. We spent the summer of 2014 coming up with all sorts of ideas to grow the business. It was basically a collegial sharing of ideas that created the trust among us. I’m now doing the same thing with a company called AGXactly (2021 Startup Challenge Venture Division Winner). I helped them put their pitch together. They’re combining the best of computer vision, which is a specialty of mine, and artificial intelligence on a drone delivery platform to monitor the health and productivity of large agricultural fields. I think they have terrific potential.
It’s important to have a good sense of perspective. There are some companies you might want to mentor, but don’t really have the skillset or the industry experience. So, I’ve convinced myself to walk away from some opportunities where I really didn’t think I could add the value that they needed, and it would be better left to somebody else who had more domain expertise.
Why would you recommend iiED for mentorship?
If you look at the beginning with the Startup Weekend, going through the Startup Challenge, and the Community Capital Expo, they offer a whole process. They aren’t isolated competitions, they’re ongoing processes— even if you don’t win, you learn something.
The quality of the advisers at iiED is pretty significant, whether it’s professional services like accountants and lawyers, or more general business people like myself. The iiED is itself a center of entrepreneurship and business excellence. Businesses like Yoderm/Apostrophe have demonstrated that the process really works.
Speaking of Apostrophe, can you share any stand out experiences working with entrepreneurs at Startup Challenge?
The passion and enthusiasm of the teams, and their willingness to listen and accept new ideas. Midway through the Yoderm/Apostrophe journey, we decided to completely pivot from offering dermatology services to creating a compounding pharmacy to deliver our own private label drugs and eliminate middleman costs. It was a significant strategic decision, which I was a little bit reluctant to endorse at the beginning. Once we got together and understood the full dimensionality, even though it seemed like a huge challenge and a big risk, we embraced it. The willingness of entrepreneurial teams and their boards and their advisors to pivot as circumstances demand, is a critical success factor.
It’s not just the companies that come out of the iiED experience, it’s all the collateral businesses that benefit from having that kind of an incubator here. How many of those companies went out to restaurants? How many of them went to movies and dry cleaners and how much ancillary revenue came into the community by virtue of having an incubator here that was fostering startup companies? How many new jobs were created? Lots of different metrics that point to the fact that this is a real stimulus to growth of our local economy.
How does iiED produce coachable entrepreneurs?
I think iiED’s programs help people better understand business. When I was an undergraduate, “business” was sort of a dirty word. If I’d had a program like iiED, I could have said, “This is fun.” I think the startup phase of a company is the most exciting. It’s the most difficult, but the most fun because there are no hierarchies, there aren’t any rules, you’re creating your own culture. And everybody’s in there pitching in, doing all sorts of things that they didn’t expect they would be doing. That’s where you get to really understand how to build a culture and comradery.
It also helps entrepreneurs gain exposure, get to know people, and become willing to accept advice. Some people at the beginning are defensive because they don’t want their idea to be poached or impinged on, which is natural. I remember feeling that way, but I realized that there are people here that genuinely want to help, and I embraced that.
It’s primarily about trust and acceptance. The entrepreneur has to trust the mentor and the mentor has to feel confident that the entrepreneur is receptive to the idea. The ideas may not all be right, but at least have a discussion about it. I’ve always found that making a bad decision is better than making no decision at all. At least with a bad decision, you can learn from your mistake and pick yourself up. If you just do nothing, you don’t learn.
How do you think that iiED helps create startups that are worth investing in?
iiED filters those companies who are not ready to move to the next step. It encourages them to step back and says, “Let’s figure this out before we keep going.” Particularly with apps. It’s really easy to develop an app. It doesn’t take a lot of capital or complex programming. But you don’t realize all the steps that need to come after that in terms of the product. Do you have a sales strategy? Do you know what channels are important? Do you really understand the competitive differentiation you have? Do you understand what it takes to really scale the business?
So, At the end of the iiED process, they’ve been vetted and coached. When they present to an investor, the investor can say, “Oh, they came out of iiED. I know that they’re going to be worth looking at because they’ve been coached at every step of the way.”