Roundup of events for bootstrappers in October 2026. Online and in-person events are offered at $10.
Roundup of October 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 eight events this month to help you move your business forward. Join us as your interests dictate and schedule permits. You can sign up here to get the monthly roundup of events for Bootstrappers
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 1 8:30 am CDT Chicago Bootstrappers Breakfast (Online)
https://www.meetup.com/bootstrappers-breakfast-chicago/events/315567523/
Fri Oct 2 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
Weds Oct 7 8:00 am PDT Mastermind Open House https://www.meetup.com/skmurphymastermind/events/gmwjztyjcnbkb
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”
Weds Oct 7 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 Pilot Projects Fail: 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. In this talk, the speaker draws on 35 years of experience spanning early neural network research, genomics AI startups, consulting, and enterprise transformation projects to explore why that gap persists and what organizations can do about it.
The 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.
Rather than offering hype or fear, this talk provides a grounded, experience-based perspective on where AI and large language models are genuinely useful today and where they still require structured systems, governance, and human oversight.
Attendees will gain practical frameworks and guidance for making AI a sustainable organizational capability.
About Evan Steeg: 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 Oct 9 9:00 am PDT San Francisco Bootstrappers Breakfast Startups at CityGroup Center (In Person)
https://www.meetup.com/bootstrappers-breakfast-san-francisco/events/316136767
Fri Oct 16 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 20 8:00 am PDT Silicon Valley Bootstrappers Breakfast (Online)
https://www.eventbrite.com/e/silicon-valley-bootstrappers-breakfast-online-tickets-488376135167
Fri Oct 30 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 August
Meaning before detail: avoid premature elaboration. This is a hard test and forces you to explain things in your customer’s language and in the context of the problem they are trying to solve or the job they are trying to get one. It requires you to use “customer language” to describe what you can do for them, first at a high level, and then adding details in response to their questions. It’s also legitimate to ask them questions, even if only to clarify their situation and view of their needs. Both parties should be asking questions, or it can become an interrogation; an effective sales call or demonstration is driven by mutual curiosity.
Effectuation or Effectual Entrepreneurship is a model developed by Saras Sarasvathy from interviews with experienced and successful entrepreneurs. Here are some blog posts and chalk talks on it:
- Chalk Talk: Sarasvathy’s Effectuation Model for Startups
- Saras Sarasvathy’s Effectual Reasoning Model for Expert Entrepreneurs
- One Mistake Entrepreneurs Make: A Great Product Will Sell Itself
Sell the result: Successful startups don’t ask early customers to pay until they have delivered the result they promised. This type of offer pulls all of the risks to the startup’s side of the table. Now they can have a conversation about the value of what you are promising, separate from a discussion about the probability that you can deliver it–or that the customer will be able to accomplish a task using your software. There are two unknowns they are wrestling with:
- What result can the startup guarantee?
- How much do they need to change their business processes and workflow to take advantage of your product? Their calculation of the total cost of your product includes the amount of behavior and process change they will need to make to get the full benefits you promise them. See also https://www.skmurphy.com/blog/2014/01/24/q-how-to-pull-the-trigger-on-a-pricing-model/
Early customers are a risk reducing milestone. They enable references, case studies and other proof that you can deliver value. You should be prepared to provide a lot more service to early customers to deliver the results you promised and to offer “introductory” or “pioneer” pricing. A simple model of customer journey is understand-believe-act. The references attack the “believe” hurdle.
In the beginning, you must do things that don’t scale. You may have several hypotheses for what your startup will look like at scale but in the beginning you will be doing a lot of improvisation to test your theories and deliver a result that leads to a referenceable sale.
Don’t focus solely on obstacles and constraints. It can be frustrating to talk to many prospects and fail to close any deals. Prospects will give you many reasons why they won’t buy; some are true, many are not. If you have tried something a half-dozen or a dozen times and it hasn’t worked, you need to change it up. Pay close attention to what generates interest, and find ways to build on it. This doesn’t mean you have to give up on the vision you have for your product and your startup, but you may need to find prospects who are interested or adjust your offer for the people who will talk to you.
- https://www.skmurphy.com/blog/2025/01/23/micah-boster-on-market-insertion/
- https://www.skmurphy.com/blog/2016/02/13/am-i-making-a-fool-of-myself/
- https://www.skmurphy.com/blog/2021/03/20/what-to-do-when-you-are-asking-yourself-is-my-product-meh/
- https://www.skmurphy.com/blog/2020/06/26/how-to-leverage-current-business-assets-for-growth/
Lightning Round Question for October 2026
What’s the best advice another founder gave you?
Trademarks: “Bootstrapper Breakfast” and “Entrepreneurs Who Eat Problems For Breakfast” are registered trademarks of SKMurphy, Inc.
Image Credits: “Entrepreneur-computer” on Pixabay by Alyibel-3625842used with permission.
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