Dirt Talk by BuildWitt: “Letting People Go (BuildWitt Update #23)” — DT 383

Date: October 20, 2025
Host: Aaron Witt

Episode Overview

In this candid BuildWitt Update, Aaron Witt reflects on a challenging week for the company—one marked by the difficult decision to let seven team members go. Through personal anecdotes, transparency, and an unwavering commitment to BuildWitt’s mission, Aaron dives into the realities of steering a business through change, financial pressures, and the high cost—personally and organizationally—of making tough personnel decisions.

Key Discussion Points & Insights

1. The Bigger Purpose of BuildWitt (00:12–02:16)

• Aaron redirects common misconceptions about BuildWitt (“Isn’t this just Aaron with some cameras?”) and explains its multifaceted mission:
  • Changing the dirt world for the better
  • Building the next generation of the industry
  • Major initiatives include the Ariat Dirt World Summit and BuildWitt Improve (a software product for civil construction training).
• The aim of these Monday episodes: keep listeners informed about real, behind-the-scenes happenings—good, bad, or indifferent.

“Part of that is also storytelling—what I do like on podcast, YouTube, social media, etc. So hopefully these shorter Monday editions give you some insight as to what the heck is going on in the business and what it is that we do.” (00:57)

2. Radical Transparency & This Week’s Big News (02:16–04:30)

• Aaron considered two possible approaches to this update:
  • Share only the positive, or
  • Tell the truth about letting people go.
• Staying true to the company’s core value, “Transparency wins.”
• Decision: Be upfront about “letting some seven people go”—a significant portion of their team.

“I could have acted like everything was gravy ... but to the left was the other path. That was the truth. Write about what really happened this week. The big news, as uncomfortable as it may be ... Transparency wins is a core value for a reason here at BuildWitt.” (01:44–02:32)

3. BuildWitt’s Early Years: Growth Fueled by Investment (04:30–09:10)

• The story of financing:
  • Early struggles with cash flow led to a loan (which became equity) from Randy, an industry veteran.
  • Additional growth funded by investments from construction industry leaders and Caterpillar dealer principals.
• Aaron uses a vivid analogy:
  • “We were the fat kid in the upper-class friend’s pantry, going nuts with all the snacks” (05:46)—they spent enthusiastically, hiring quickly, thinking little was impossible.
• The sense of fun and boundless optimism was eventually tempered by reality—a slow slide into “quicksand.”

“We merrily skipped along. We hired a lot of people. We were shouting from the rooftops, having a grand time ... until we ran, skipped, walked our way into quicksand.” (07:31)

4. The “Quicksand” Metaphor & Resetting the Business (07:35–10:48)

• Cartoon quicksand: The more you panic, the deeper you sink; the process was years in the making.
• Reflects on the exhaustion and difficulty of getting out.
• Today’s focus:
  • Growing as a profitable software company with true market value.
  • Moving away from reliance on outside capital—winning “with our own money.”

“Quicksand you can only free yourself from it once you calm down and act carefully but deliberately ... Today ... we were finally freeing ourselves from the quicksand.” (08:35)

• Excitement about the future: self-reliance, sustainability, and a company true to its mission.

“Winning is way cooler than using somebody else’s money. So the future ... is way cooler than anywhere we’ve been and way more exciting.” (11:29)

5. Commitment to the Mission Despite Change (10:49–13:15)

• BuildWitt’s mission hasn’t wavered since day one:
  • Serving the dirt world
  • Building the next generation
• Acknowledges criticism but insists: “the mission has never changed, and it won’t.”
• Many changes in the business model, but not in purpose.

“The one thing I don’t think anyone can criticize with any merit is that we have been consistent when it comes to our mission ... I've been dead on with that since day one ... it won't change because I genuinely believe that is my purpose.” (12:15–13:01)

6. Difficult but Necessary Retooling (13:15–16:42)

• Past six months: Deep questioning and repositioning after selling their creative agency, Fieldwork.
• BuildWitt is now purely a people business—no physical assets, just its team—making transitions particularly painful.
• To achieve profitability (“which is safety for the overall team”), every expense was re-examined, and with 80% of spending tied to people, cuts were unavoidable.
• Cuts were not driven by poor performance but by changing business needs. Some roles couldn’t be maintained in the new structure.

“Everyone we let go over the past week is a great human being ... But they were either in positions we couldn't maintain or that weren't performing at the new standard, and this is far less them and much more us as a business ...” (15:37–16:16)

7. Investing in the Future & the Bittersweetness of Change (16:42–20:12)

• Even as seven were let go, the company is hiring for six new positions, mostly in sales and software development.
• The reality of leadership: “It’s not just business, it’s people’s lives, livelihoods ... your empathy grows, it doesn’t get easier—it gets harder.”
• Aaron shares his internal conflict: rationally recognizing the necessity, but emotionally struggling with the impact.
• Experience helps gauge when decisions are “right,” even if it doesn’t feel right in the moment.

“It’s just business, quote unquote. But it’s not just business, it’s people’s lives, livelihoods.” (18:15)

“Where we're going could not be more right for our overall team, our customers, the industry, our mission—even if it doesn't feel like that sometimes.” (19:22)

8. On Leadership, Communication, and Transparency (20:12–End)

• Leadership in high-performing organizations requires making tough decisions and continual team evolution.
• Acknowledges previous shortcomings in internal communications, but strives to be “transparent with all of you as well.”
• Offers a direct line for feedback: “You can believe whatever you want to believe, but that’s at least my side of the story ... If you ever have comments, questions ... reach out to me anytime.” (22:49–23:05)

Memorable Quotes & Moments

• On transparency and leadership:

  “Transparency wins is a core value for a reason here at BuildWitt.” (02:29)

• On the hardships of layoffs:

  “So everyone we let go over the past week is a great human being. Great human being. But they were either in positions we couldn't maintain or that weren't performing at the new standard, and this is far less them and much more us as a business ...” (15:37–16:16)

• On the evolution of the business:

  “The future, and I can see the future ... is way cooler than anywhere we've been and way more exciting.” (11:29–11:44)

• On making tough calls as a leader:

  “Those are the decisions that anybody in a high performing world makes ... to get them to the next level, to make the changes they have to, to get them to where they need to be ultimately. And that's what we're doing.” (21:21–21:49)

Important Timestamps

• 00:12 – Opening and BuildWitt’s true scope
• 01:44 – Choosing the path of transparency
• 04:30 – Financial background and “fat kid in the pantry” analogy
• 07:35 – Entering the “quicksand”
• 10:49 – Reaffirming the mission
• 13:15 – Selling Fieldwork and resetting the business model
• 15:37 – Layoffs and staff restructure
• 16:42 – Hiring forward, the emotional cost of layoffs
• 18:15 – “It’s not just business, it’s people’s lives”
• 20:12 – Leadership lessons and communicating the changes
• 22:49 – Invitation for feedback and sign-off

Tone & Takeaways

• Honest, confessional, and unscripted—Aaron’s voice is both vulnerable and certain, granting listeners privileged insight into the pains and hopes behind difficult business decisions.
• A valuable listen for anyone interested in leadership, entrepreneurship, and the realities of pivoting a company in pursuit of its mission.