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.
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 to, used for AI training data, which may be surfaced by competitors through prompts or queries. There is also a raft of new privacy regulations that apply more stringent tests to people under 18, especially those under 13.
- It’s tempting to say, “I am looking for people who have this need.” But if it’s not a need they will naturally disclose in public forums, social media, or on a business website, you need to consider how you will actually find them, because they are effectively “in hiding.” It may be easier to target firms that are natural condensation points for people or firms with that need instead. Often, trusted advisor firms like accountants, attorneys, or specialty service firms will routinely come into contact with the problem you solve. Consider flipping your focus to equipping them with tools to help their customers or clients. If I am in training to be an electrician or a plumber, the schools may know who I am, but it may be hard to reach me directly. If you have a tool that helps select a bridal dress, it may be better to sell to bridal stores or wedding planners, who will see a steady stream of engaged women.
- Don’t look for “beta testers’ look for early customers. See https://www.skmurphy.com/blog/2012/04/02/a-beta-customer-is-not-a-tester-or-a-user-but-an-early-customer/ for other problems with viewing prospects as testers instead of potential customers.
- Bootstrappers often discover they are going after customers in a market served by an established firm or set of firms. It’s hard to enter a market where you have fewer resources and less credibility than your competitors unless you can take advantage of a change or discontinuity that they have not adjusted to, have proprietary knowledge or expertise they lack, or have a business model that is attractive to at least a niche and they cannot embrace without losing more money from current customers than they will gain entering the niche.
- A change or discontinuity in the market they have not reacted to. This might be a new technology, a change in customer taste or values, or other changes in the environment.
- A unique or at least not widely appreciated insight or perspective that allows you to build a better product for at least a subset of the market and create a niche. Peter Thiel calls this “a secret,” a fact or insight that is contrary to common wisdom that is true for at least a niche.
- A business model that the incumbent cannot copy because it does too much damage to their existing revenue stream. For example, a hotel that caters to business travelers that has a high end bed and free breakfast but skimps on a lot of other amenities (these exist).
- Security concerns are really trust concerns: unless they are specifically asking for support for a particular protocol or set of protocols you need to address your credibility. You cannot substitute technology for a root concern about your credibility.
Lightning Round Question for May 2026
Who is already trying to solve this without me and how can I insert myself there?
Trademarks: “Bootstrapper Breakfast” and “Entrepreneurs Who Eat Problems For Breakfast” are registered trademarks of SKMurphy, Inc.
Image Credits: “Rubiks-Cube-Puzzle” on Pixabay by Jaijujacob-14010912 used with permission.