Roundup of events for bootstrappers in December 2025. Online and in-person events are offered at $10.
Roundup of December 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 eleven 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 Dec 2 12:00 pm PST Drop-In Mastermind for Non-Fiction Writing
https://www.meetup.com/skmurphymastermind/events/312072570/
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.
Tues Dec 2 9 am PST Vegas Bootstrappers Breakfast Roundtable (In Person) The Coffee Press
https://www.meetup.com/bootstrappers-breakfast-las-vegas-startups/events/311748791/
Wed Dec 3 8:00 am PST Mastermind Open House https://www.meetup.com/skmurphymastermind/events/312074238/
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.
Wed Dec 3 11:00 am PST / 1:00 pm CST / 2:00 EST Lean Culture: Influencing Executives’ Decisions with Data
https://www.meetup.com/lean-culture/events/311752372/
Data scientists and change agents often find themselves producing valuable insights that don’t make it to the decision table. Not because their data or evidence is wrong, but because the message doesn’t land. This talk explores how teams doing research and analysis can communicate their findings more effectively to executive decision-makers.
Participants will learn to frame analyses in business terms, translate technical metrics into impact language, and deliver insights that drive action. We’ll explore how to align with executive priorities: strategy, risk, opportunity, revenue, and cost. Jeff Allison will share real-world examples and practical frameworks.
Key takeaways include:
- Understanding the executive mindset
- Framing the problem in business terms
- Telling a clear, action-oriented story
Fri Dec 5 9:00 am PST Silicon Valley Bootstrappers Breakfast (In Person) Redwood City
https://www.eventbrite.com/e/bootstrappers-breakfast-in-redwood-city-for-silicon-valley-founders-tickets-1963668317799
Fri Dec 12 9:00 am PST San Francisco Bootstrappers Breakfast Startups at CityGroup Center (In Person)
https://www.meetup.com/bootstrappers-breakfast-san-francisco/events/311879100/
Tues Dec 16 8:00 am PST Silicon Valley Bootstrappers Breakfast (Online)
https://www.eventbrite.com/e/silicon-valley-bootstrappers-breakfast-online-2024-tickets-488376135167
Wed Dec 17 11:00 am PST / 1:00 pm CST / 2:00 EST Lean Culture: AI That Works: Workflows for Clearer Outreach (Today)
https://www.meetup.com/lean-culture/events/311859426/
Founders don’t need more AI “tricks.” They need clarity. This session is about using AI to think better — not hide behind it. We’ll cover three low-friction workflows that help you write messages people actually respond to:
- How to open an email so a tired reader keeps reading
- A quick framing tool to get clear about the ask
- A 60-second tone check so your outreach feels human and honest
This is practical and hands-on. Bring a message you need to send — we’ll improve a few together
About John Nash: John Nash is an educational leadership professor and solopreneur who helps builders use AI to produce clearer, faster, more ethical communication. He teaches design thinking and researches applied AI at the University of Kentucky.
Thurs Dec 18 8:30 am CST Chicago Bootstrappers Breakfast (Online)
https://www.meetup.com/bootstrappers-breakfast-chicago/events/cpkzjtyhcqbxb/
Fri Dec 19 9:00 am PST Mtn View Bootstrappers Breakfast at Red Rock Coffee (In Person)
https://www.eventbrite.com/e/mountain-view-bootstrappers-breakfast-tickets-1200388748059
Tues Dec 30 9:00 am PST 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 November
-
- Sales has a lot of failure so even smoothly functioning firms are winning, at best, half the proposals. Plan accordingly for ongoing setbacks and failures. In the beginning it’s as much a struggle for sensemaking. This also means you should never take one shot to break through. I think most tactics or individual attempts have a 10-20% success rate. This means you should budget for three to five tries, with intelligent variation, before abandoning an approach.
- Even paying experts is like managing volunteers; expertise must be enlisted, it cannot be commanded.
- Nothing lasts longer than an interim solution (variation on a Russian proverb)
- Boring lucrative educational — pick two https://www.skmurphy.com/blog/2015/08/10/pick-boring-or-grinding-over-losing-money/
Lightning Round Question for December 2025
As you look back on the past year, were some of your goals too ambitious or unrealistic? Have any unforeseen changes disrupted your initial plans?
Trademarks: “Bootstrapper Breakfast” and “Entrepreneurs Who Eat Problems For Breakfast” are registered trademarks of SKMurphy, Inc.
Image Credits: “Maze-labyrinth-puzzle-mystery” on Pixabay by Gustavorezende used with permission.