Michael Wolfe Founder Coaching
Let's Build a Great Startup
I am a Startup Coach based in San Francisco, CA. I have spent my 35-year career founding five startups and helping other founders. I love the startup world, want more startups to be founded, and I want more of those to succeed.I focus on helping technical founders who are learning how to be a CEO or CTO. My ideal profile is a startup that has reached some level of product/market fit but now has to build a great company to make the most of the opportunity.
My Story
I started my career at Stanford, where I got a BS and MS in Computer Science in 1991, with a focus on artificial intelligence. I was a teaching assistant or lecturer for four years, including running the legendary CS198 teaching program. I worked for startups over the summer.I then worked for Goldman, Sachs in New York and London, building derivative trading systems. I loved the thrill of working elbow-to-elbow with the users of my products.I came back to San Francisco in 1994 and joined I/PRO as the first employee and Director of Engineering. I/PRO was the world's first web analytics company and may have been the world's first SaaS product. I/PRO was acquired by Engage in 1998.In 1996 I joined Kana as the first hire and VP of Engineering. We pioneered the web contact center market, reaching $150M revenue in four year, acquired four companies, and reached a $15 billion market cap
on NASDAQ.I joined Benchmark as an Entrepreneur in Residence in 2002, leading to my co-founding Vontu. We pioneered the Data Loss Prevention market, growing to $50M in revenue and a $350 million acquisition by Symantec in 2007. I joined Symantec as the CTO of the Enterprise Product Group, focusing on launching the DLP business globally and merger integration.In 2009 I returned to Benchmark and founded Pipewise, a CRM platform for subscription businesses. We shut the company down after we failed to reach product/market fit and took a much-needed sabbatical, moving to Barcelona Spain, where I spent the year traveling, mountain bike, working with local startups and guest lecturing at ESADE business school.In 2015 I co-founded Gladly, an AI-powered customer service platform for retailers. Gladly has raised over $200 million and powers customer service for leading brands like Nordstrom, Crate and Barrel, Ulta, REI, and Warby Parker. I retired from Gladly at the end of 2024.In addition to my work as a founder, I have angel invested in about 20 startups and served on the advisory board of about 25 more. I am also a Board Partner at Point Nine Capital, where I have worked with portfolio companies like Typeform, Contentful, and Loom. I also mentor seed-stage founders at StartX, Entrepreneurs First, and the Lean Launchpad program at Stanford.
How I Work
The fit between coach and founder is crucial, so we start with a quick chat to get to know each other and explore if there is a fit. I love meeting founders, so I am always happy to have these calls, even if you are only in the early stages of exploring what you need.If we decide to work together, I invest upfront time to get oriented. I find I work best when I have the full picture, so I like to meet some of the key people, understand your business, and sit in on a few meetings. I also also use these meetings to build and deliverWe then agree we can work on based on what I heard. We agree to work on a few projects that are most critical to helping you build a great company. We track progress and hold each other accountable.We’ll schedule a bi-weekly 1-1 to work together, and I’ll also devote time to ad hoc or asynchronous interactions between meetings as needed.
Writing and Speaking
I enjoy writing and speaking about startups. You can find my Substack at nextfounder.co, where I discuss challenges that founders face at every stage of their startup. I also wrote extensively on Quora in their earlier years.I also enjoy speaking in front of audiences.
Reach out!
I always love to connect with founders, so please reach out. You can find me on LinkedIn or [email protected].