In this episode, host Jason Seward sits down with Tom Olson — licensed general contractor, investor, developer, and founder of multiple real estate businesses operating out of Gary, Indiana. With over 2,000 transactions, 1,200-plus flips, 700 investor rentals, and 45 mid-term rentals under management, Tom has built one of the most vertically integrated real estate operations in the Midwest — and he did it with a mission at the center: flip the city of Gary, Indiana, and make it a place people move to instead of from. Tom's story starts at 12 years old swinging hammers, runs through the 2008 crash that took him from $120K to $20K in income overnight, and culminates in a multi-company empire guided by clear core values, business operating systems, and asset leaders running each vertical. This episode covers business structure, goal setting, knowing your numbers, the danger of scaling too fast, and why most real estate investors are solopreneurs masquerading as business owners. What You'll Learn in This Episode How Tom built a vertically integrated real estate business from construction roots — and why he never let go of the contracting side The two reasons most real estate businesses fail: not knowing their numbers and scaling faster than their systems can handle How to structure a multi-company operation using asset leaders, core values, and quarterly goal reviews Why your business is not an asset unless it operates without you — and how to close that gap What Tom means by "flip the city of Gary" and how a God-given vision shapes every business decision he makes Timeline Highlights [1:03] – Introducing Tom Olson: 2,000+ transactions, 1,200 flips, and a mission to transform Gary, Indiana [3:13] – How Tom and Jim Ingersoll met on an IRA cruise — and discovered they were both from Jamestown, New York [9:04] – Starting in construction at 12 years old and why he never wanted to let it go [9:48] – How Rich Dad Poor Dad introduced him to the idea of cash machines — and sparked his investing journey [12:01] – The 2008 crash: going from $120K to $20K overnight and making cold calls for the first time [12:35] – The investor who told him he was the first contractor in 30 years to show up on time, quote on the spot, and finish on budget [14:54] – Wholesaling 1,300 to 1,400 homes between 2009 and 2015 with a partner [15:12] – How the partnership split led to building every vertical himself: construction, property management, brokerage, and lending [18:31] – Why not everyone should have 11 businesses and 43 employees — and why that's okay [19:41] – Scaling Up and Traction: the two books that changed how Tom ran his companies [21:26] – Which businesses are actually sellable assets and which are just jobs with an LLC [24:06] – Moving his family to Gary, Indiana during the crash — and the moment God gave him the vision to flip the city [26:24] – Why every business decision must fit inside two goals: give to missions and transform Gary [29:05] – SMART goals, quarterly rocks, and why you should never reach all your goals [33:43] – Core values as a hiring filter: charity, stewardship, community, growth — and the 20-minute onboarding video that weeds people out [37:05] – The three departments every business has: sales, operations, and admin — and why sales is always most important [39:59] – Why payroll over 50% of gross profit is a warning sign you cannot ignore [43:42] – The two reasons businesses fail: not knowing numbers and scaling too fast [49:52] – Why scaling too fast turns businesses into Ponzi schemes — and how to know when to hit the brakes [54:11] – What real profit actually means: you've been paid back, the business pays you a salary, and it's consistently profitable quarter after quarter Rapid Fire Highlights Show up, do what you say, answer the phone: Tom's formula for winning 80% of sales without marketing Vision drives everything: every business must fit inside giving to missions and flipping Gary, Indiana — if it doesn't fit, let it go Biggest failure red flags: not knowing your numbers weekly and scaling before your systems, people, and processes are ready Core value litmus test: if you're a lone wolf, a know-it-all, or unwilling to be held accountable, you won't last in Tom's companies Real business vs. solopreneur: if the business stops when you stop, you don't own a business — you own a job Resources Mentioned Elite Dealmakers community discounts: elitedealmakers.com/discount This episode is sponsored by 608B Capital: https://608bcapital.com/ Gary Dealmaker National Conference — October 1–3, 2026 (garydealmakerevent.com) Active Turnkey Podcast — Tom's podcast on buying rentals the right way Conduit Capital — Tom's hard money lending fund for accredited investors Good Success — Tom's real estate and consulting platform: goodsuccess.com Traction by Gino Wickman Scaling Up by Verne Harnish The One Thing by Gary Keller Good to Great by Jim Collins It's Okay to Be the Boss by Bruce Tulgan Connect and Subscribe If this episode sparked something for you, subscribe, leave a review, and share it with someone who's serious about building their real estate legacy. New episodes every week. Dealmaker Catalyst is rooted in the culture built by Jim Ingersoll and the nationwide Dealmaker community.
