Roundup of events for bootstrappers in June 2026. Online and in-person events are offered at $10.
Roundup of June 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.
Tues Jun 2 12:00 pm PDT Drop-In Mastermind for Non-Fiction Writing
https://www.meetup.com/skmurphymastermind/events/314772899/
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 Jun 4 8:00 am PDT Mastermind Open House https://www.meetup.com/skmurphymastermind/events/314802661/
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 June 5 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 Jun 9 9:00 am PDT Vegas Bootstrappers Breakfast Roundtable (In Person) The Coffee Press
https://www.meetup.com/bootstrappers-breakfast-las-vegas-startups/events/314313359/
Weds Jun 10 11:00 am PDT / 1:00 pm CDT / 2:00 EDT Lean Culture: Subscription Engines for CPG: Which Model Fits Your Brand?
https://www.meetup.com/lean-culture/events/314909732/
Subscriptions aren’t one thing. They’re a category of mechanics, and the right one depends on your product, margin structure, and how your customers actually buy. In this session, Igor Krasnykh explores the main subscription engines CPG brands can apply (replenishment, curation, access/membership, build-your-box, and hybrid models) with real examples of who each one works for and the operational tradeoffs behind them. Igor is the founder of IdealData, an eCommerce intelligence platform that replaces passive dashboards with proactive, real-time business signals for merchants.
Fri Jun 12 9:00 am PDT San Francisco Bootstrappers Breakfast Startups at CityGroup Center (In Person)
https://www.meetup.com/bootstrappers-breakfast-san-francisco/events/314581751/
Tues Jun 16 8:00 am PDT Silicon Valley Bootstrappers Breakfast (Online)
https://www.eventbrite.com/e/silicon-valley-bootstrappers-breakfast-online-tickets-488376135167
Thurs Jun 18 8:30 am CDT Chicago Bootstrappers Breakfast (Online)
https://www.meetup.com/bootstrappers-breakfast-chicago/events/wthdwtyjcjbxb/
Fri Jun 19 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
Weds Jun 24 11:00 am PDT / 1:00 pm CDT / 2:00 EDT Lean Culture: From Lab to Market: 35 Years of Closing the AI Gap
https://www.meetup.com/lean-culture/events/314691205/
Why AI Pilots Fail — and What To Do Before You Start One
For more than three decades, AI practitioners have faced the same fundamental challenge: bridging the gap between what works in the lab and what delivers reliable value in the real world. This session introduces a practical framework for evaluating AI readiness across leadership, strategy, data infrastructure, platforms, and skills before launching major initiatives. It also examines the most common reasons AI projects fail, including poor problem selection, underestimated data challenges, lack of operational accountability, and ignored organizational impacts.
Evan Steeg is an AI researcher, biotech entrepreneur, and innovation strategist specializing in ethical AI, synthetic biology, and commercialization, with degrees from Cornell and a PhD in Computer Science from the University of Toronto, where he studied under Nobel winner Dr. Geoffrey Hinton.
Fri Jun 26 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
- One way to demonstrate proof of value or proof of efficacy is to charge by the bug found if your product can identify problems or defects in a system. You can do a free scan, disclose a third of the problems you have found, and then say they can pay for the rest. You want to offer a flat fee or per-seat fee that allows them to run it on a regular basis, as this pricing model does not capture the peace of mind that flows from knowing that no defects were detected. But as a door opener, charging by the bug can pull the risk to your side of the table.
- Customer discovery is tricky because you must be excited about your product to persevere. But if conversations don’t spark customer interest, you have to tinker. My rule of thumb: if, after 15-20 conversations with real practitioners or domain experts, no one responds to an offer or suggests what’s missing for them to try or evaluate, you need to make adjustments.
- If you are engaging in customer discovery, you have to make real offers that promise a particular result for a price. Asking folks, “would this be valuable for you?” or “Would you use this?” invites predictions that rarely come true. Instead, offer a proof point and ask them if they would pay.
- A team new to an industry or discipline can create a breakthrough because they approach it with “newcomers eyes” and try concepts that “everyone knows” don’t work, but put a spin on them that makes them viable. However, such a team always benefits from at least one domain expert to avoid basic mistakes or misunderstandings that newcomers are subject to.
- There is a temptation that introverted engineers can fall prey to: they continually update their website and see if they get form fills or inquiries. In the beginning, it’s much more effective to build a one-page pitch or short deck (e.g., six slides) you can share with prospects. That allows you to make changes after each conversation and watch if a prospect’s eyes glaze over as you ask questions.
Lightning Round Question for June 2026
What inspired you to start your business? What is the story behind your journey?
Trademarks: “Bootstrapper Breakfast” and “Entrepreneurs Who Eat Problems For Breakfast” are registered trademarks of SKMurphy, Inc.
Image Credits: “Yellow-Bulb-Idea” on Pixabay by Motionstock used with permission.