Becker Private Equity & Business Podcast

January Founder of the Month: Brian Taylor of Thinkspan

Date: December 4, 2025
Host: Scott Becker
Guest: Brian Taylor, Founder & CEO of Thinkspan

Episode Overview

In this episode, Scott Becker interviews Brian Taylor, founder and CEO of Thinkspan, as the “January Founder of the Month.” The discussion delves into Taylor's entrepreneurial journey, the origins and ambitions of Thinkspan, leadership and team-building philosophies, risk-taking, and the future of personal information management. Taylor shares firsthand stories, leadership lessons, and insights into building deep-tech innovations, making this episode compelling for entrepreneurs, technologists, and business leaders.

Key Discussion Points & Insights

1. Brian Taylor’s Background & Entrepreneurial Journey ([00:29]–[04:19])

• First Podcast Appearance: Taylor’s debut discussing Thinkspan and his ventures.
• Kernel Seasons Origin: Founded a successful popcorn seasoning company—became the #3 blended seasoning brand in the U.S., then exited to pursue new ideas.
  • “Some people call me a serial entrepreneur, but… really, I fancy myself a permanent beginner. I love being in new positions and kind of navigating brand new, imaginative products.” ([00:37])
• Inspiration for Thinkspan: Motivated by wanting to efficiently pass life information to his children, struggling with existing tools like Dropbox/Evernote.
• Permanent Beginner Mindset: Embracing new industries and remaining curious.

2. What Is Thinkspan? Vision, Approach & Technology ([01:43]–[07:25])

• Deep Tech Approach: Reimagining personal information management; creating a private, intelligent data “fabric” that lives on the device rather than the cloud.
• Patents & AI Integration: Comprehensive patent portfolio, including proprietary personal AI concepts predating the AI boom.
  • “We’ve been kind of ahead of our time… skating to where the puck is going, as they say.” ([02:40])
• Privacy by Design: All data end-to-end encrypted; even Thinkspan never sees what users store.
• Command & Control Center: Positioned as a “personal operating system” that adapts and self-organizes user data.
• Initial Focus: Direct-to-consumer super-app that consolidates information now scattered in dozens of apps or physical locations.
  • “We’re over half a century into the information age and the problem of personal information management still hasn’t been solved.” ([05:44])
• Beta Status & User Retention: Product currently in beta with promising retention metrics.

3. Market & Customer Focus ([04:19]–[05:07])

• B2C Launch; B2B Roadmap: Currently focused on consumers, with a future vision for enterprise partnerships, connecting personal and corporate data fabrics.
  • “Right now it's like 40-plus apps in one… within a year or two, it'll be hundreds, if not thousands.” ([04:35])
• Future Opportunities: Seamless, encrypted collaboration with professionals (e.g., accountants).

4. Real-World Utility & Differentiation ([05:07]–[07:25])

• Pain Points Addressed: Scattered personal documents, passwords, estate planning, etc.
  • “People that we talk to, it’s nearly unanimous: personal information management is a mess.” ([06:25])
• Self-Organizing Information: Use-case: Auto-detecting & connecting important documents (like tax K-1 forms), tying them to relevant entities securely.
  • “You put the information into Thinkspan and things magically happen… in total privacy.” ([07:09])

5. Leadership Lessons & Inflection Points ([08:05]–[13:26])

• Entrepreneurial Inflection Points: Leaving Kernel Seasons—a leap of faith; learning to trust instincts and talent in others.
• Unorthodox Path: From philosophy major to entrepreneur, then later, business school for confidence and network.
• Letting Go as a Leader: The growth that comes from empowering talented teams to take ownership.
  • “It’s hard, especially when you see a very talented person who may do something differently than I would do, but also realizing, holy smokes, they're right and they’re actually doing it better.” ([11:01])
• Hard-Earned Lessons: Trusting gut feelings, learning to move decisively, embracing mistakes for growth.

6. Calculated Risk & “Walt Disney Theory of Business” ([16:29]–[21:20])

• Approach to Risk: Build with optionality—platform thinking provides multiple paths to success and reduces risk.
• Bold vs. Incremental: Recommends deep commitment (“big & bold”) over tentative, minimal investments.
  • “One thing also that de-risks something is to do it big enough and bold enough that you’re really doing something different, not just making an incremental change.” ([17:28])
• Turning IP into Advantage: Broad patents allow Thinkspan flexibility—can pivot into new markets (military, ad tech, insurance, etc.).
• Venture Studio Vision: Potential to spin out verticals based on Thinkspan’s foundational technology.

7. Culture, Team-Building & Long-Term Vision ([21:20]–[24:53])

• Promote from Within: Retain talent, build trust and autonomy—“friends on an adventure” dynamic.
  • “I like to say in my businesses… I want it to feel like we're friends on an adventure… serious, but we're friends.” ([23:34])
• Balance of Fun & Seriousness: Intentionally non-stuffy environment, intellectual challenge, a shared mission, and enjoyment.
• Sacred Obligation: Team sees Thinkspan as meaningful, non-trivial work; stewardship of people’s most vital information.

8. Looking Ahead — 2026 & Beyond ([24:53]–[27:31])

• Next Steps: Shifting from R&D to scaling; growing with user feedback and strong retention.
• AI Integration: The next phase is making personal, private AI available to users; currently in advanced development.
  • “It’s going to be really exciting when people see… what happens when people can take their private information and have a private intelligence reason over it.” ([26:50])
• User-Centric Growth: Not scaling for scale’s sake; focusing on quality, cost-effective user acquisition, and real-world value.

9. Personal Habits & Staying Centered ([27:31]–[30:04])

• Work-Life Balance: Family, physical wellness (sleep, diet, exercise), and time in nature are all critical to sustaining high performance.
• Team as Support System: Dispersed, global Thinkspan team—mutually supportive, aligned on mission, diverse perspectives.
  • “We gain strength from each other and everyone supports each other… as long as everyone is aligned on the mission and bringing their own strengths…” ([29:20])

10. Michigan Sports — A Lighthearted Finish ([30:04]–[31:13])

• Michigan vs. Ohio State: Taylor good-naturedly pivots to hope in basketball when questioned about the football rivalry.

Notable Quotes & Memorable Moments

“Some people call me a serial entrepreneur, but… really, I fancy myself a permanent beginner.”
— Brian Taylor ([00:37])

“We're over half a century into the information age and the problem of personal information management still hasn’t been solved.”
— Brian Taylor ([05:44])

“One of the challenges of the business right now is… to convince people of how our technology works and how secure we are. The good news is once people realize this is totally different, they're in.”
— Brian Taylor ([06:34])

“It’s hard, especially when you see a very talented person who may do something differently than I would do, but also realizing, holy smokes, they're right and they’re actually doing it better.”
— Brian Taylor ([11:01])

“Trust your instincts. If you kind of have a nagging feeling… about something, if it's not the right person or project or strategy, there's generally something real behind that.”
— Brian Taylor ([12:14])

“One thing also that de-risks something is to do it big enough and bold enough that you’re really doing something different, not just making an incremental change.”
— Brian Taylor ([17:28])

“I want it to feel like we're friends on an adventure… we’re serious, but we’re friends.”
— Brian Taylor ([23:34])

“We're done. We'll always be working on the instrument, but we now get to play music with the instrument that we've created.”
— Brian Taylor ([14:32])

Important Timestamps

• Brian’s Story & Thinkspan’s Origins: [00:29]–[04:19]
• What Thinkspan Does (Deep Tech & Privacy): [01:43]–[07:25]
• Customer/Market Focus Discussion: [04:19]–[05:07]
• Self-Organizing Info & Differentiation: [07:25]
• Key Inflection Points in Career: [08:05]–[13:26]
• Leadership Lessons & Letting Go: [11:00]
• Calculated Risk & Product Philosophy: [16:29]–[21:20]
• Culture & High-Trust Teams: [23:04]–[24:53]
• Looking Ahead to 2026: [24:53]–[27:31]
• Personal Habits & Staying Centered: [28:10]–[30:04]
• Closing (Michigan/OH State banter): [30:04]–[31:13]

Resources & Connect

• Thinkspan Website: thinkspan.com
• Available on: iOS and Android (search "Thinkspan")
• Contact Brian Taylor: LinkedIn — open to conversations about Thinkspan

Tone & Style

The episode is engaging, optimistic, and transparent—the guest is candid about his journey, lessons learned, and ongoing curiosity. Both Becker and Taylor exchange in a conversational, friendly manner, blending practical strategy with big-picture thinking and moments of self-deprecating humor.

This episode offers an in-depth look into the intricacies of founding and scaling a deep tech company, with actionable lessons on leadership, risk, and building products that can adapt as the world changes.