Episode Overview

Podcast: Making It with Jon Davids
Episode: 217 - "We Had The Biggest Clients... and Here's Why We Lost Them"
Guest: Brian Hamilton, Chairman of Live Switch, Founder of Sageworks
Date: October 3, 2025

In this episode, Jon Davids speaks with Brian Hamilton about the journey of building Sageworks from scratch into a $100M tech company, tackling the triumphs and painful lessons learned along the way. The focus centers on how winning massive enterprise clients (Citibank, Intuit, Wells Fargo) didn't yield the expected success, leading to a crucial pivot that ultimately defined the company. Brian shares candid insights into entrepreneurship, self-awareness, and the importance of honest self-examination for founders.

Key Discussion Points & Insights

1. Brian Hamilton’s Non-Traditional Entrepreneurial Journey

• Background: Brian started in banking and finance but quickly moved to entrepreneurship, stressing that practical experience outweighed formal credentials.
  • “I was a practitioner, I was an entrepreneur… that was really kind of the magic there.” (00:21, Brian)
• Co-Founder Dynamic: His co-founder handled the tech while Brian developed the logic and algorithms behind Sageworks' offerings.

2. Building the Product & Early AI Innovation

• Massive Initial Effort:
  • Brian wrote "10,000 pages of single space text" over two years to build their financial analysis engine (an early form of AI).
  • Reports automatically condensed complex analysis into a “one sheeter”—useful for any business owner.
• Early AI Roots:
  • “It was really, truly early AI and I know more about that than most people. And I don't know as much as I should, but yeah, it was early, very early.” (01:19, Brian)

3. The Big Breakthrough—And Unexpected Roadblock

• First Major Clients:
  • Sageworks landed early licensing deals, most notably with Citibank (via a cold Yahoo search) and later with Intuit and Wells Fargo.
  • “It’s just those moments you live for because you’re like, oh my God, you know, my work is actually worth something.” (03:10, Brian)
• Licensing Business Model:
  • Initially, the core business was licensing to large institutions:
    • Jon: “Was the business model licensing to big orgs?”
    • Brian: “Yes, that’s exactly right. Oh, by the way, a little footnote. It didn’t work.” (04:08 – 04:19)
• Reality Check:
  • These partnerships with banking and accounting giants turned out not to fit as seamlessly as hoped. The core operations of large clients didn’t align with Sageworks’ offering.
  • “What we found is that… Citibank is a bank and they loan money… Their core business, no matter what they say, is not doing financial analysis.” (04:45, Brian)
  • The deals were large in dollar terms but failed to drive meaningful adoption or impact.

4. The Emotional Challenge of Business Model Failure

• Expectation vs. Reality:
  • The pain of landing prestigious contracts, only to realize—and admit—they weren’t working.
  • “It’s very difficult to start a business and not know whether you’re going to make any money… but what’s harder is when you get the deals and then they don’t turn out to be what you think they are… That’s really demoralizing.” (05:18–05:27, Brian)
• Jon’s Empathy:
  • Jon relates with his own experience: after years of dev, clients wanted something entirely different than what was built.
  • “We built this thing out to function in one way and we realized, oh crap, guys, remember that last three years we've been working, it’s a whole different thing now. So let’s start from square one.” (05:27, Jon)

5. The Pivot: From Enterprise to SMBs

• The Turning Point:
  • Brian shares that real success came not from big enterprise deals, but from shifting focus to serving small accounting firms.
  • “So what I did is I did a side move and I had a little tiny team of two people… go out and sell to small accountant firms… that became the core business. Isn’t it fascinating?” (09:35–10:22, Brian)
• The “Side Project” That Became The Company:
  • Jon: “So that, that little side project became the main driver. It was in the end, the small accounting firms that actually needed this. And the Citibanks didn’t need this.” (10:22, Jon)
  • Brian: “That’s right. Exactly.” (10:32, Brian)

6. Entrepreneurship, Self-Awareness, and Honest Feedback

• Mindset & Adaptation:
  • “Entrepreneurs are crazy... It’s a matter of taking data in all the time, integrating that data and pivoting. And if you cannot do that quickly... you can’t usually survive as an entrepreneur.” (06:43, Brian)
  • “Most times, as you know, John, you get it out there, you listen to the customer and you pivot. And that takes time.” (07:27, Brian)
• Self-Examination:
  • Listen to your gut and be brutally honest about product/market fit—no matter external validation or initial revenues.
  • “There’s always a voice inside of you… Listen to the voice.” (08:46–09:33, Brian)
• Putting Yourself in the Customer’s Shoes:
  • “Go to the other person. If I were running the company, what’s the value of the technology, really?... Be the other person. I can’t tell you how important that is.” (12:04–12:48, Brian)

Notable Quotes & Memorable Moments

• “You work hard, and if you work hard enough, you’ll get these moments where you get a big deal and you feel validated. It was huge.” (03:26, Brian)
• “But honesty is one of them. And so, inside of me I’m like, ah, I don’t know, man. I’m not feeling it… So what I did is I did a side move… And it worked.” (09:35, Brian)
• “You just got to have it. …There are people listening right now that maybe the revenues are there, maybe they’re getting a lot of accolades, but they know that they're not quite a fit yet. It’s that level of self-awareness.” (11:49, Jon)
• “We persuade ourselves all the time that the things that we create are wonderful… But be the other person. I can’t tell you how important that is.” (12:04–12:48, Brian)

Timestamps for Major Segments

| Timestamp | Segment / Quote | |---------------|-----------------------------------------------------------------------------| | 00:21 | Brian on background: “I was a practitioner, I was an entrepreneur…” | | 01:19 | Early AI foundations | | 03:10 | Landing Citibank; “It’s just those moments you live for…” | | 04:14 | Licensing business model. “Oh, by the way… it didn’t work.” | | 04:45 | Why enterprise clients weren't the right fit | | 05:27 | The frustration of misfit deals (Jon and Brian share stories) | | 06:43 | On the need for entrepreneurs to pivot and adapt quickly | | 09:35 | Inside the pivot to small accounting firms | | 10:22 | Jon/Brian on the “side project” becoming the core business | | 11:49 | Jon on the importance of self-awareness for founders | | 12:04–12:48 | Brian’s advice: “Be the other person” |

Overall Tone

Candid, insightful, and practical—Brian and Jon openly dissect setbacks and pivots, steering the conversation beyond business tactics into the deeper virtues of humility, adaptability, and listening. The chemistry is collegial, and both speakers give examples, offer humor, and strive to leave listeners with actionable wisdom rooted in real experience.