Michael Wolfe Founder Coaching
Let's Build a Great Startup
I am a Startup Coach based in San Francisco. I have spent my 35-year career founding five startups and helping other founders. I love the startup world, want more founders to start startups, and I want more of them to succeed.I focus on helping technical founders who are learning to be a CEO or CTO. My ideal client is a startup that has a product and some customers and now has a chance to build a company to make the most of the opportunity. We help founders with:• Maintaining the personal motivation, health, and energy needed to handle the hard work and difficult times that all founders face.
• Aligning company and product strategies, including finding a focused Ideal Customer profile, positioning, value proposition, and product roadmap.
• Building a lightweight but powerful planning process that aligns the team around a handful of the most important goals.
• Building a high-performance product team, including cross-functional alignment between engineering, product management, product design, and peer groups like Sales and Customer Success.
• Hiring great people, handling bad hires, and building a transparent, high-performance culture.
• And, of course, some of my best conversations just come from asking what’s on a founder's mind in a given week and being a sounding board to help them work through the issues of the day.
My Story
1986 – 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.1991 – Joined Goldman Sachs in New York and London, building equity derivative trading systems. I loved the thrill of working elbow-to-elbow with the users of my products in a high-paced environment.1994 – Returned to San Francisco 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 1998.1997 – Joined Kana as the first hire and VP of Engineering. We pioneered the web contact center market, reaching $150M in revenue in four years, acquired four companies, and reached a $15 billion market cap on NASDAQ.2001 – After a sabbatical, I joined Benchmark as an Entrepreneur in Residence, 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. I joined Symantec as the CTO of the Enterprise Product Group, focusing on merger integration and launching the DLP business globally.2009 – Returned to Benchmark and founded Pipewise, a CRM platform for web subscription businesses. We shut the company down after failing to reach product/market fit, learning many valuable lessons. My family took a much-needed sabbatical in Barcelona, where I spent the year traveling, mountain biking, working with local startups, and guest lecturing at ESADE business school.2015 – 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.I have invested in about 20 startups and have 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 explore if there is a fit. I love meeting founders, so I am always happy to meet you, even if you are just starting to explore what help you need.If we decide to work together, I invest some 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 use these meetings to build and deliver initial feedback on how you can increase your leadership capacity.We then agree to focus on a few areas that are most critical to helping you build a great startup. We track progress and hold each other accountable.We’ll schedule a bi-weekly 1-1 to work together and 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. See my pieces on Train Like a Startup Athlete and Activate Founder Mode to get a sense of my philosophy.I also wrote extensively on Quora in their earlier years.I enjoy speaking in front of audiences of startup founders and their teams. I’ve given talks focused on:
• Building your “Operating System” to keep your company aligned and motivated to pursue a handful of the most important goals.
• Becoming a “Startup Athlete” by investing in your personal health and productivity, making you more effective at home and at work.
• Theory X and Theory Y management, which asks if you are building and managing your team from a place of trust and empowerment.
• When to deploy “Founder Mode” to make sure the work your company delivers is excellent.
• How to build a transparent culture to keep your team motivated, informed, and working on the right things.
Reach out!
I always love to connect with founders, so please reach out. You can find me on LinkedIn or [email protected].