Day 2 – Breakout Session 4 – 9:45-10:15 AM
Room: Wildfire
Pride Is Going to Be Your Downfall
Joshua Thompson · RizeCon 2026 · Pocatello
Joshua Thompson bought a trailer park in Pocatello for $880,000 in April 2017. It had 60 lots, 16 homes, and eight of those homes had holes in the floor with trees growing up through them. Over five years, he built it from $6,000 a month in revenue to $37,000 a month, from 8 livable homes to 57, and sold it in February 2022 for $3.45 million.
Two weeks later, his best friend — the property manager — called to say the new owners had raised lot rents from $374 to $425 a month. Nobody moved out. Joshua did the math. He hadn’t left any money on the table. He had left the table.
By the time the buyers raised rents again, the property was valued at over $5 million. The lot rent today is $480 a month. In 2022, he had negotiated a three cap — an almost unheard-of number in today’s seven-cap market. He had been generating $13,000 a month in mailbox money and thought he was maximizing the asset. He wasn’t. He never asked anyone what they would do. That is the whole talk.
What he covered
Know your blind spots — and find people who can see them. The lesson Joshua draws from the trailer park story is not about cap rates or NOI calculations. It’s about the specific failure mode of working alone, staying in control, and never asking the question “What would you do?” He had a property manager. He paid him 6% to handle operations. And then every day, he still drove through the park, still stopped at the mailbox, still photographed every check to send to the accountant. He wasn’t delegating — he was cosplaying at delegation while holding every lever himself.
Don’t have one mentor — have many. When the “one-hit wonder” comment landed (a longtime acquaintance called him that to his face after the sale), Joshua’s response wasn’t defensiveness. It was to start asking questions to a lot of different people about a lot of different things. He doesn’t have a single mentor. He has a network of people he reaches out to on specific problems. When he listed a $1.1 million property and the market was slow, he called John Earl, CEO of Keystone National — a $2.5 billion private credit firm in Salt Lake — and asked him: you’re someone who could afford this house; what would make you buy it? John rewrote the marketing. The first person who came in bought it. Joshua did not do anything except ask the right person the right question.
Your mentor doesn’t have to announce they’re your mentor. Roger Akers, founder of Akers Financial, came to Idaho State University as an executive in residence. Joshua was in a dark period after the sale and the one-hit-wonder comment. He showed up skeptical. Faculty started texting him: “This guy’s talking about everything you know.” Within two hours of conversation — honest, open conversation from someone Joshua would have expected to be unapproachable — Roger had offered to let him invest in one of his tech companies. They bought 1% of it. That relationship taught Joshua what mentorship actually looks like: someone who doesn’t need to be asked to mentor you, who is generous with their knowledge, and who acts like a peer while knowing significantly more.
Control is a trap dressed up as professionalism. Joshua names it directly: the problem with the trailer park was not the strategy. It was that he couldn’t let go. He had done the work, built the thing, and then couldn’t stop being in it even after hiring someone else to be in it. The first man who poked him in the chest and told him “Pride is going to be your downfall” — the buyer of his first business, Shows Theater Design — was right then, and right again for the trailer park exit. Pride shows up not as arrogance but as the quiet need to be the one who knows, the one who controls, the one who’s in the room.
Your employees are mentors too. If you’re leading by reaction — firefighting instead of strategizing — the problem is usually that you haven’t built the trust structures that would let you step back. Your employees have ideas. They’ve been there. They see things you don’t. Joshua argues for giving them a voice and for carving out time every week to think about the business rather than just running it. “If all I would’ve done is that” — taken time to strategize — “I would’ve seen the math.”
AI as a mentor, accountability partner, and financial analyst. Joshua pushed back gently on the earlier session’s recommendation to avoid Claude Code, because it’s where he lives. His Claude Code agents each have names they chose themselves. Vega is his investment analyst — argues with every investment decision, sends him a market email at 6:30 every morning, picks apart his portfolio. Atlas is his navigator — reviews everything he writes, asks questions until he has to justify his own reasoning to himself. He ran his entire debt consolidation strategy through Vega, brought the output to a banker, and negotiated a refi at 5.99% that reduced his monthly payments, saved $1,100 a month in interest, and left him in first position on every property except one. His accountant now receives a plan and the relevant tax code citations before touching the books. He pays $7,000 a year for a signature.
What attendees got
Joshua offered to share his full slide deck and to walk anyone through the Claude Code setup he described. His contact information was on his closing slide. He also offered a detailed AI use case for anyone who wants to see Vega’s daily market email or the prompting structure he uses for financial analysis.
His practical recommendation for running AI locally: don’t use your main computer. Get a separate machine — he uses a 15-year-old Mac Mini he bought at Costco. A Raspberry Pi also works if the processing requirements are modest. Keep your sensitive financial data local, not on cloud-based services. Build your agent prompts to be pages long and specific. Save everything in Markdown files, not Word documents, because AI reads them faster and more accurately.
One story that landed
He sold the trailer park for $3.45 million. Two weeks later, his best friend called. The new owners had raised rents. Nobody moved out. He did the math. In 90 days, the new owners had pushed the value to over $5 million by doing one thing he had never thought to do: ask what the market could actually bear. He had lowered rents during COVID out of care for his tenants — a decision he doesn’t regret. But he had never asked a commercial banker, never asked a real estate attorney, never asked anyone in his network what they would have done. He thought he was maximizing the asset because he knew it better than anyone. He didn’t know what he didn’t know.
“Pride is going to be your downfall.” — Said to Joshua Thompson by the buyer of his first business, and remembered ever since
“We need to remember that we don’t know everything. We need to ask for help.” — Joshua Thompson
About the speaker
Joshua Thompson teaches at Idaho State University’s College of Business, where he runs business pitch competitions and brings practitioners into the classroom as executives in residence. Outside of teaching, he owns commercial properties, rental properties, and short-term rentals in the Pocatello area and at Bear Lake. He holds multiple licenses including real estate and securities certifications, and has built, exited, and reinvested across several industries over the past two decades. His first business was Shows Theater Design, which he started after getting hurt playing ball at ISU.