Roundup of events for bootstrappers in October 2025. Online and in-person events are offered at $10.
Roundup of October 2025 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 nine 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.
Thurs Oct 2 8:00 am PDT Mastermind Open House https://www.meetup.com/skmurphymastermind/events/308287988/
Fri Oct 3 9:00 am PDT Silicon Valley Bootstrappers Breakfast (In Person) Downtown Campbell
https://www.eventbrite.com/e/bootstrappers-breakfast-in-downtown-campbell-tickets-215740344177
Tues Oct 7 12:00 pm PDT Drop-In Mastermind for Non-Fiction Writing
https://www.meetup.com/skmurphymastermind/events/311091217/
Writing a business book or a blog? Join our non-fiction writers group of similarly minded small biz 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.
Fri Oct 10 9:00 am PDT San Francisco Bootstrappers Breakfast Startups at CityGroup Center (In Person)
https://www.meetup.com/bootstrappers-breakfast-san-francisco/events/jjsqstyhcnbnb/
Thurs Oct 16 8:30 am CDT Chicago Bootstrappers Breakfast (Online)
https://www.meetup.com/bootstrappers-breakfast-chicago/events/cpkzjtyhcnbvb/
Fri Oct 17 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 Oct 21 8:00 am PST Silicon Valley Bootstrappers Breakfast (Online)
https://www.eventbrite.com/e/silicon-valley-bootstrappers-breakfast-online-2024-tickets-488376135167
Weds Oct 22 11:00 am PDT / 1:00 pm CDT / 2:00 EDT Lean Culture: Using AI to Make Smarter Bets: Forecasting & Decision-Making
https://www.meetup.com/lean-culture/events/310863691/
Innovation always feels like a gamble—especially when you’re bootstrapping. The difference between a good bet and a bad one can mean the life or death of your business. Yet too many founders rely on gut instinct.
This session will show you how AI can help small business owners make smarter, leaner decisions without losing flexibility. We’ll explore how AI-powered forecasting can help you decide where to invest your time and money, giving you credible ranges and probabilities for outcomes instead of false certainty.
We’ll tackle the real challenges SMB founders face, like:
- How do you forecast realistically when you don’t have much data?
- How can you use AI to quickly test assumptions and avoid wasted spend?
- How do you stay agile without getting lost in dashboards and complexity?
About Tristan Kromer: Innovation coach and founder of Kromatic, Tristan Kromer, has helped innovation teams, leaders, and startup ecosystems globally. With experience as a startup entrepreneur and corporate product manager,. Tristan has supported a diverse set of organizations, including nonprofits like ChildFund and big brands like Unilever and Salesforce. Collaborating with over 30 tech accelerators such as Innovation Norway and Vinnova, he also donates time to offer free consultancy to budding entrepreneurs.
Fri Oct 31 9:00 am PDT Silicon Valley Bootstrappers Breakfast (Online)
https://www.eventbrite.com/e/silicon-valley-bootstrappers-breakfast-online-2024-tickets-488376135167
Key take-aways from the Bootstrappers Breakfast conversations in September
- Your Early Customers Can Determine Your Trajectory, If not your Fate. Getting clarity early on who you want to serve is essential. Serious customers looking to grow their business or significantly expand their capabilities are superior to those who are lackluster and lukewarm. Their feedback, along with what you can learn from their experiences and unfolding understanding of their needs, enables you to develop a better product.
- It’s easier and faster to join a community rich in target customers than to try to create or cultivate one. “Communities already exist…think about how you can help that community do what it wants to do.”? Mark Zuckerberg (quote from slide 29 of Neil Perkins’ slide show “What’s Next in Media “)
- Beware the seduction of the Swiss Army ?Knife, or worse, the Swiss Army Chainsaw. ?The minimum is to identify the two or three blades that are essential to your customer; the better approach is to build an icepick. Focus can be a source of great success as it can increase quality (much less unnecessary functionality to? develop, debug?, and maintain) and lower barriers to adoption by virtue of a simpler interface.
- ?Why You, Why Now? Two good questions you should answer up front and revisit ?periodically as you learn more.? What’s changed recently you can take advantage of. What trends are already established that you can leverage. How can you build on your unique capabilities and experiences?
- You have to know how long it takes your customer to see value. Many products that are able to effect significant transformations in a business require complex setup and can take weeks to a month or two to see an impact. You need to minimize setup costs and time to value realization and help your customer sustain effort and investment until they see a payoff.
- Word of mouth is an important component of growing a business. You have to deliver value, make distinct and memorable promises that you are able to keep, and develop good long-term business relationships with customers and partners.
Lightning Round Question for October 2025
Any there any areas of your business that’s obsoleted?
Trademarks: “Bootstrapper Breakfast” and “Entrepreneurs Who Eat Problems For Breakfast” are registered trademarks of SKMurphy, Inc.
Image Credits: “Film Photograhy Negatives” on Pixabay used with permission.