MSIV Welcomes 2022 Startup Advisor in Residence

Q &A with Mike Lewis

Tuesday, January 25, 2022, from Corte Madera, CA

Today, we are very excited to announce that Mike Lewis, a serial startup founder and entrepreneur, is joining Marin Sonoma Impact Ventures as our first Startup Advisor in Residence (STAIR) for the 2022 calendar year.

Mike joins the MSIV community having founded and successfully exited three startup companies over the past 20 years. His full bio can be found here. In his role as MSIV’s STAIR, Mike will be providing members of the MSIV North Bay Founder Network with advice, startup-school curriculum, mentorship, and strategy as these founders progress their entrepreneurial journeys.

In June 2020, Mike was one of five North Bay startup founders to attend the inaugural meeting of the MSIV North Bay Founder Network when the MSIV movement was in its nascent stages. Since then, Mike has exited his Marin-based startup, and we are so excited for his engagement with MSIV to come full circle as he now works to ‘pay it forward’ to this next group of North Bay entrepreneurs.

MSIV Founder & Managing Partner Zachary Kushel sat down with Mike to discuss his learnings in entrepreneurship and all that is ahead as he more deeply engages with this growing startup community.

ZK:  We're all very excited to collaborate with you. What gets you so excited about helping entrepreneurs on their journeys?

ML: I’ve co-founded three startups and I’ve learned that, when you’re just getting started, there are lots of challenges. With my experience, and with the help of my current colleagues, I’ve now been able to solidify my lessons learned the hard way into repeatable frameworks that tie together across companies. As a founder, you end up asking the same questions over and over – what’s my go to market? How do I hire a sales team? How do I fundraise?

The reality is that being a founder is one of the few jobs in the world where there is no curriculum, no playbook. Sure, there are lots of blog posts – but what’s most common for founders is the equivalent of wanting to fly an airplane and getting thrown in a plane without any instruction and expecting that they’ll be able to fly. It’s all really trial and error, and in the startup community, if that plane crashes and burns, the community oftentimes comes back and gives you another plane! With these frameworks, I aim to help founders execute faster and better, which allows them to focus on their core differentiation as a company rather than the basics.

ZK:  You’re a three-time founder and exited each time – you did not suffer the fate of dying on the vine like a majority of startups. Other than being lucky, which is a great attribute to have, what can you share that allowed you to ensure a successful outcome on each of these journeys?

ML: For my first two companies, we had to pivot very hard. What we launched didn’t work, and as you suggest, we were dying on the vine.

My first company, Qloud, was a music discovery service, and in 2006 we were offering a way for listeners to uncover new music without any ability to listen to music through our service. What listeners wanted was the ability to listen to music, on-demand, with unlimited streaming, for free. So, we pivoted to offer this, and within six months, we had 10 million monthly users on the service, which set us up for a successful outcome.

My second company, Kapost, started as a service for journalists at a time when publishers were letting go of full-time journalists and hiring freelancers – this was 2010, around the time the Huffington Post model really began to take off. We had a business that was working, and publications loved our service, but there weren’t nearly enough of them, and they weren’t able to pay us much because their business models were under stress. At the same time, content marketing was emerging as a trend, so we leaned into this market and went after B2B customers that had the budget to spend with us.

ZK: For founders, I talk about this as being steadfast, stubborn, and opinionated, but also flexible enough to know when it’s time to pivot. 

ML: You need to be intellectually honest about your company, and I think a lot of founders don’t want to admit when things aren’t working. You either have product-market fit, or you don’t, and if you don’t, that’s okay, you just have to keep working on it. Oftentimes you’ll talk to entrepreneurs and you’ll get the “everything’s going great” line even when they are close to dying on the vine. The problem with this is you are better off telling people what you’re having problems with because then you are much more likely to get solutions.

ZK: You experienced hypergrowth at a later-stage startup in Airbnb. How did working at a larger startup inform the way you think about being a scrappy early-stage founder?

 ML: I joined Airbnb when they were close to 500 people and left when the company had over 5,000. It was a fantastic experience, and I got to work with so many high-quality people – we were hiring all the time. I got to see up-close what real excellence looks like in a profession, whether in design, sales, or any function. Because of this excellence, and since you have a tremendous amount of resources, you’re not forced to wear a lot of hats, whereas with a small startup, you do everything.

If you’re a product manager at a small startup, you talk to the customers, you do the market research, you look at the data, you’re the support team, you’re uncovering the bugs, you’re managing engineers, you do it all. The large startup PM does none of that because they have a team that does design, a research group, a data scientist, everything you can think of. I think small startup operators who’ve seen that mature startup excellence up close who can have that in the back of their mind as they’re executing on each of these roles can be more effective.

ZK: In June 2020, you attended the first-ever meeting of the MSIV North Bay Founder Network when you were running Onward out of Mill Valley. Tell us about how you’ve seen this community come together over the past 1.5 years and what you see ahead.

ML: I remember that meeting very well, and it was eye-opening to meet you and learn about the MSIV movement and your vision for this community’s future. I never fully appreciated how many incredibly talented people there are living in this community, and I remember thinking to myself in that meeting the other attendees are great, they are my neighbors, and I’ve never met them and how much I wanted to change that.

When I moved to the Bay Area at the end of 2014, I moved directly to Marin and drove to San Francisco to commute to Airbnb every day. Funnily enough, I thought I was the only person doing this. Over the years that followed, I realized that I was far from alone, and that there are thousands of people in this community who have incredible experience working at iconic companies and who have embarked on their own entrepreneurial journeys across Marin + Sonoma. If we can just connect with one another, we can learn from each other and build our own unique, strong community. It’s inevitable, and it’s so powerful, and it’s why I’m so excited to be a part of this and do my part to help North Bay entrepreneurs on their journeys.

Elizabeth Murphy is the Vice President of Community at Marin Sonoma Impact Ventures.

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