Roundup of May 2026 Bootstrapper Events - BootstrappersBreakfast

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Roundup of events for bootstrappers in May 2026. Online and in-person events are offered at $10.

Roundup of May 2026 Bootstrapper Events

We offer online events for bootstrappers including Bootstrappers Breakfast and Lean Culture. There are also in-person Bootstrapper Breakfast meetings in Las Vegas, San Francisco and Silicon Valley. These events are for "entrepreneurs who eat problems for breakfast."®

We have ten events this month to help you move your business forward. Join us as your interests dictate and schedule permits.

Are you an entrepreneur who’d like to share lessons learned?  If you’ve a reached a milestone in your entrepreneurial journey and would like to share lessons learned, please contact Theresa Shafer (tshafer@skmurphy.com) to explore scheduling a short briefing at a Bootstrapper Breakfast or a talk at a Lean Culture event. You must have attended a Bootstrapper Breakfast or Lean Culture event to be considered.

Fri May 1 9:00 am PDT Silicon Valley Bootstrappers Breakfast (In Person) Redwood City

https://www.eventbrite.com/e/bootstrappers-breakfast-in-redwood-city-for-silicon-valley-founders-tickets-1963668317799

Tues May 5 12:00 pm PDT Drop-In Mastermind for Non-Fiction Writing

https://www.meetup.com/skmurphymastermind/events/314301102/

Writing a business book or a blog? Join our non-fiction writers group of similarly minded small business folks where we can keep each other motivated and accountable. Each attendee will have a chance to share a short piece (500-1,000 words) by reading it aloud or providing access to a google doc or emailing other attendees to get feedback. We do this every mastermind session.

Thurs May 7 8:00 am PDT Mastermind Open House https://www.meetup.com/skmurphymastermind/events/314334592/

Who sees your blind spots first? Clients, customers or trusted peers? Learn how a group of trusted peers can give you an extra competitive advantage in your business. This is an open house meeting to get your questions answered about what’s involved in an SKMurphy Mastermind and meet others who are considering joining. See also “Masterminds Help Founders with Empathy, Feedback, and Follow-Through”

Fri May 8 9:00 am PDT San Francisco Bootstrappers Breakfast Startups at CityGroup Center (In Person)

https://www.meetup.com/bootstrappers-breakfast-san-francisco/events/313043381/

Weds May 13 11:00 am PDT / 1:00 pm CDT / 2:00 EDT Lean Culture: The Mechanics of Grant Funding: Fit, Clarity, and Credibility

https://www.meetup.com/lean-culture/events/313964156/

In this practical session, Paul Scott breaks down the mechanics of winning grants, moving beyond high-level advice to the details that actually make a difference. Drawing on real-world experience, he will walk through how to identify the right opportunities, align your proposal with funder priorities, and present a clear, credible plan for execution.

Attendees will learn how to define problems in a way reviewers understand and structure proposals for clarity and impact. Paul will also share common pitfalls that lead to rejection. Whether you’re new to grant writing or looking to improve your win rate, this session offers actionable guidance you can apply immediately.

Paul Scott has been a technical writer for over 20 years. He uses his training and experience as a scientist to help clients convey highly technical information to customers and investors. He writes white papers and blog articles, as well as grant proposals for academic research and the Small Business Innovation Research (SBIR/STTR) program. He has helped his customers get grant awards from DARPA, NSF, NIH, the Department of Energy and other federal programs. He lives and works near San Francisco.

CANCELLED – returning in June: Thurs May 14 9:00 am  PDT Vegas Bootstrappers Breakfast Roundtable (In Person) The Coffee Press

https://www.meetup.com/bootstrappers-breakfast-las-vegas-startups/events/314313359/

Fri May 15 9:00 am PDT Mtn View Bootstrappers Breakfast at Red Rock Coffee (In Person)

https://www.eventbrite.com/e/mountain-view-bootstrappers-breakfast-tickets-262928394907

Tues May 19 8:00 am PDT Silicon Valley Bootstrappers Breakfast (Online)

https://www.eventbrite.com/e/silicon-valley-bootstrappers-breakfast-online-tickets-488376135167

Thurs May 21 8:30 am CDT Chicago Bootstrappers Breakfast (Online)

https://www.meetup.com/bootstrappers-breakfast-chicago/events/314382868/

Fri May 29 9:00 am PDT Silicon Valley Bootstrappers Breakfast (Online)

https://www.eventbrite.com/e/silicon-valley-bootstrappers-breakfast-online-tickets-488376135167

Some key take-aways from Bootstrappers Breakfast conversations in April

Privacy, confidentiality, and access to proprietary data and intellectual property are increasingly salient concerns. This can apply to bug reports filed with a vendor or to content that an application has access...