"Trust your instinct—we're a startup." - Alex Lee
In this episode of Tech Scenes, Jeff James Martin sits down with Alex Lee, CEO and Co-founder of Truewind, to talk about the evolution of AI in accounting, the lessons learned through Y Combinator, and how trusting your gut can be a superpower in startup leadership. A former aerospace engineer turned entrepreneur, Alex shares how Truewind is streamlining bookkeeping and financial modeling for accounting firms by building a digital staff accountant powered by AI and supported by concierge service.
The conversation covers everything from the messy realities of fundraising and team dynamics to the powerful role of community in the startup journey. Alex breaks down how open communication, structured thinking, and constant experimentation are critical in navigating early-stage growth. The episode also dives into the balancing act of following instincts while remaining flexible and data-informed—and how Truewind is just scratching the surface of AI’s potential to transform accounting.
Key Takeaways:
Instincts matter—especially when data is incomplete or the path forward isn’t clear.
Truewind is building an AI-powered digital staff accountant to support accounting firms.
The founder’s transition from aerospace to accounting tech shows how transferable deep problem-solving skills can be.
Y Combinator offers immense value through its resources, mentorship, and founder community.
Fundraising is unpredictable; transparency and vulnerability with investors can foster better outcomes.
Team alignment requires clear roles, open communication, and regular OKR reviews.
A support system for founders—whether mentors or peers—is essential for staying grounded.
Experimentation is key to finding product-market fit, and focus helps avoid distractions.
The future of AI in accounting is still unfolding, but Truewind is leading the charge.
YouTube Chapters:
00:00 – Trusting Instincts in Startups
01:17 – Introduction to Truewind
02:15 – The Vision Behind Truewind
04:17 – The Journey from Aerospace to Accounting
08:11 – Experiences in Y Combinator
10:20 – Benefits of the YC Program
12:17 – Fundraising Experiences and Lessons Learned
16:31 – The Reality of Startup Challenges
19:03 – The Importance of Open Communication
24:03 – Navigating Team Dynamics and Responsibilities
30:13 – Experimentation and Focus in Growth
36:02 – Instinct vs. Data in Decision Making
38:14 – The Future of AI in Accounting
Resources:
Learn more about the book Peak Teams – Mastering the Habit of Unstoppable Venture-backed Companies https://a.co/d/hp5Jtnu
Visit Collective Genius™ to Build Your Venture-backed Team with the Peak Operating System™ https://www.collective-genius.com/
Music by Andrew Applepie https://soundcloud.com/andrewapplepie
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