Dirt Talk Podcast: Brian Anderson of Bear Construction — DT 394

Date: November 27, 2025
Host: Aaron Witt (A)
Guest: Brian Anderson (B), President of Bear Construction

Episode Overview

In this candid conversation, Aaron Witt sits down with Brian Anderson, founder and president of Bear Construction in Middle Tennessee. The episode dives deep into Brian’s entrepreneurial journey—how he started Bear Construction in 2019, the lessons learned “in the ring,” cash flow discipline, leadership evolution, faith integration, and intentional transparency about business realities. The discussion is frank, relatable, and packed with valuable advice for anyone in construction or business.

Key Discussion Points & Insights

1. Starting from Scratch: The Bear Construction Origin Story

• [00:49] Brian describes the company’s inception in 2019. Dissatisfied working for someone else (“filling up my diesel truck and his card would decline”), Brian was motivated by necessity and family responsibilities.
• The Name “Bear”:
  • The company name was chosen by his wife, inspired by their family (“name it Bear because you’re my bear”).
  • Quote: “So I asked my wife, ‘What do I name this company?’ She’s like, ‘Name it Bear because you’re my bear.’ So I was like, all right.” — Brian [01:33]
• Bootstrap Beginnings:
  • Started with no equipment, using his wife’s 2008 Kia Spectra and his dad’s old truck, hiring family members for help.
• “I had three guys and we went and did this work for that contractor.” [04:05]

2. Early Days: Water Services and Pipe Work

• [04:38–07:00] Brian explains water service installation in layman’s terms, likening it to the human body’s circulatory system.
  • Quote: “It’s kind of like the body…you’ve got your heart, which is the water treatment plant, then…arteries, which are your big transmission lines…” — Aaron [05:18]
• Price vs Perception:
  • Water services are neither glamorous nor as cheap as developers expect. Brian details escalating costs due to city requirements and makes the case for skilled work.
  • Quote: “Builders have a mindset that should only cost me about $4,000. But most of them are 12 to 15.” — Brian [06:46].

3. Business Realities: Cash Flow, Growth, and Lessons Learned

• Cash Flow Discipline ([10:56]):
  • Quote: “It’s easier to spend someone else’s money than it is to spend your own…Every single dollar, every single penny is accounted for.” — Brian [10:56]
  • “The contractors that I’ve seen that are most successful are the most disciplined with cash and cash flow.” — Aaron [12:14]
• Employee Perception:
  • Brian reflects on how purchasing equipment is often seen by employees as him getting rich, but in reality, it’s investment for the company’s future.
  • Quote: “None of this is for me, is to grow the company to hand to my kids. They don’t see that.” — Brian [12:24]
• Exponential Growth:
  • As the company matures, Bear is bidding on large multi-phase projects (e.g., 493-house subdivisions), with 12+ projects in the works.
  • Quote: “We’re bidding 493 house subdivisions. That’s crazy.” — Brian [13:08]
• First Lawsuit:
  • Brian discusses a scope gap lawsuit and the value of detailed documentation.
  • Quote: “I’m actually no longer scared of lawsuits…now I know to document stuff.” — Brian [15:26]

4. Hiring, Training, and Building a Team

• Hard Lessons Hiring ([17:32]):
  • Brian shares stories of hiring “crackheads off Craigslist” and learning not to repeat that.
  • Quote: “I might have been able to tell you that one, though.” — Aaron [19:05]
• You Don’t Need a Perfect Plan ([19:11]):
  • The myth of needing the perfect plan before starting is debunked.
  • Quote: “That’s not how it works. Because you don’t know what you don’t know.” — Aaron [19:36]

5. Milestones: The Five-Year Mark

• Company Inflection Point ([21:22]):
  • Five years is identified as a key threshold in business maturity.
  • Quote: “Five years is kind of the breaking point where you realize, ‘all right, we’re gonna do something good with this.’” — Brian [21:22]

6. Equipment Strategy

• Buying Used, Not New ([23:45]):
  • Brian prefers buying used equipment from rental houses for reliability and cost-effectiveness, despite some small machine drawbacks.
  • Quote: “We buy used. We don’t buy anything new. We try to keep—we have a different plan than most people.” — Brian [23:45]

7. Navigating Market Challenges

• Escalating Material Costs ([30:34]):
  • Price of rock, asphalt, and other materials have skyrocketed, creating tighter budgets and challenges for contractors.
  • Contractors often end up managing subs for developers even after value engineering efforts.
• Project Delays ([35:31]):
  • Utility districts, engineering revisions, and weather all impact construction timelines.
  • Quote: “You can’t use logic anymore. You gotta start using common sense a whole lot more.” — Brian [38:34]

8. Big Business vs Small Business Friction

• Velocity & Accuracy ([41:13]):
  • Small contractors must be efficient, but are often slowed by large suppliers or partners moving at their own pace.
  • Quote: “There’s also this big difference between big business and small…for people like us, we have to deal with these bigger companies that operate on a totally different operating system.” — Aaron [40:17]

9. Leadership Evolution: No More Complaining, Leading with Faith

• Mindset Shift ([44:17], [45:20]):
  • Brian discusses spirituality’s effect on his attitude towards work and people.
  • Quote: “I realized I just hated everything about every minute of every single day… I started listening to Christian music in the car and noticed…I was smiling just riding around town, and started to…not let everything bother me.” — Brian [45:20]

10. Faith in the Workplace

• Intentional Christian Leadership ([51:17], [54:59]):
  • Brian is upfront with management hires about the faith-based culture at Bear, but isn’t pushy.
  • Quote: “I let them know in the interview that I’m a Christian man and that this company is led by Christ.” — Brian [51:17]
  • Quote: “I want people to know that…you can have your faith on the job site and in a company and not be scared to do so.” — Brian [55:06]

11. Transparency and LinkedIn Storytelling

• Building a Brand Through Honesty ([84:03], [86:13]):
  • Brian shares openly on LinkedIn—both successes and struggles—for the industry’s benefit and to connect with clients and employees.
  • Quote: “People love how honest and transparent I am about starting a company.” — Brian [84:31]
  • Posting has directly led to client relationships and trust.
  • Quote: “I’ve had a developer say, ‘I want to use you just because of what I’ve seen on LinkedIn.’” — Brian [86:13]
• Content Authenticity Over ChatGPT
  • Discussion about recognizing and avoiding inauthentic, AI-written content to maintain genuine connection.
  • Quote: “Anybody that can write and think for themselves can recognize something written by ChatGPT. You’re not fooling anybody.” — Aaron [88:14]

12. Company Growth, Delegation, and Mentorship

• Third-party Partners:
  • Brian leverages professional services (e.g., bookkeepers, HR) rather than putting strain on himself or his family.
• Recognizing Capacity:
  • Knowing his and his VP’s limits, Brian foresees bringing in more management as Bear grows.
• Mentorship:
  • Importance of direct feedback, energy, and mentorship in sustainable business growth.
  • Quote: “I love the idea of mentors. I love having someone you can call to work through something.” — Brian [122:02]

13. Practical Wisdom and Life Lessons

• On Exercise and Health ([117:00], [118:03]):
  • Both agree on the necessity of physical fitness for business performance.
  • Quote: “I can’t get to where I need to be from a business standpoint, from a life standpoint without being physically fit.” — Aaron [117:00]
• Business Ownership Boundaries ([129:29], [133:41]):
  • Brian learns he “can’t be one of the guys” as an owner, even when he wants to.
  • Quote: “I’m not one of the guys no more. I’m not one of the guys.” — Brian [129:16]

Notable Quotes & Memorable Moments

| Timestamp | Quote & Attribution | |------------|--------------------------------------------------------------------------------------| | 01:33 | “Name it Bear because you’re my bear.” — Brian's wife (as told by Brian) | | 10:56 | “It’s easier to spend someone else’s money than it is to spend your own…” — Brian | | 12:14 | “The contractors…most successful are the most disciplined with cash…” — Aaron | | 19:36 | “That’s not how it works. Because you don’t know what you don’t know.” — Aaron | | 21:22 | “Five years is kind of the breaking point…” — Brian | | 23:45 | “We buy used. We don’t buy anything new…” — Brian | | 30:34 | “It’s not gone up by, like, a little bit. It’s gone up just an astronomical amount.” — Aaron | | 44:17 | “I can’t lead that way. There’s no way I could complain about every single thing…” — Brian | | 45:20 | “I realized I just hated everything about every minute of every single day…” — Brian | | 51:17 | “I let them know in the interview that I’m a Christian man…” — Brian | | 54:59 | “I want people to know…you can have your faith on the job site…” — Brian | | 84:31 | “People love how honest and transparent I am about starting a company.” — Brian | | 86:13 | “I’ve had a developer say, ‘I want to use you just because of what I’ve seen on LinkedIn.’” — Brian | | 117:00 | “I can’t get to where I need to be from a business standpoint…without being physically fit.” — Aaron | | 129:16 | “I’m not one of the guys no more. I’m not one of the guys.” — Brian |

Timestamps for Important Segments

| Time | Segment | |----------|-------------------------------------------------------------| | 00:49 | Brian’s story of starting Bear Construction, naming | | 06:08 | Explaining water services to lay audience | | 10:56 | How Brian and Aaron manage cash flow and business finances | | 13:08 | Bidding large-scale sitework, current company scale | | 14:19 | First lawsuit experience and lessons learned | | 17:32 | Hiring mistakes and how to avoid them | | 21:22 | The 5-year business milestone | | 23:45 | Used equipment strategy | | 30:34 | Surging materials costs and changing economics | | 35:31 | Impact of delays on project schedules | | 40:17 | Big business vs small business—differences in urgency | | 44:17 | Mindset shift from complaining to leading with positivity | | 51:17 | Faith and leadership at Bear | | 54:59 | Prominence of faith in construction, not just in Bear | | 84:03 | The power of honesty and transparency on LinkedIn | | 86:13 | Social media visibility directly leading to new business | | 117:00 | Physical health’s impact on business (exercise discussion) | | 129:16 | Role change—owner not “one of the guys” anymore | | 132:19 | Handling requests for money/support from employees |

Tone & Style

The conversation is open, self-deprecating, and honest, with both Aaron and Brian sharing not just successes but ongoing struggles and lessons. There’s humor, vulnerability, and inspiration throughout—grounded in faith, community, and service. Brian’s humility and directness resonate, while Aaron’s curiosity and practical insights add depth.

Final Thoughts

This episode goes beyond construction—it delivers a compelling blueprint for entrepreneurship, leadership, and intentional culture-building. From humble beginnings with a borrowed Kia to leading a dynamic, faith-driven team, Brian Anderson embodies openness and humility. The real “dirt work” is not just the earth moved, but the lives shaped, including his own.

For more, follow Brian Anderson on LinkedIn for his transparent business storytelling, or check out Bear Construction if you’re interested in site work in Middle Tennessee.