How to Buy a $2.5M Biz and Grow it to $7.5M (with M&A)
Brian quit his corporate job to buy a tree care business older than he was.Three years later he runs a private equity backed platform of five tree care brands across three states.
Kate gets him to break down why investors are quietly buying up tree care, how he wins deals against bigger buyers, and why he spends most of his time on organic growth, not the next acquisition.
Inside the episode: the 75% margin business most people overlook, the deal that fell through days before signing, and how he found his next acquisition using AI.
Brian Instagram: https://www.instagram.com/northsidetreeprofessionals/ LinkedIn: https://www.linkedin.com/in/brian-hartman-a2a506155/
Deal Diaries with Kate YouTube: https://www.youtube.com/@dealdiaries_katechichi Spotify: https://open.spotify.com/show/033DZHytD6ER7B0qZ93TiC Instagram: https://www.instagram.com/dealdiaries_katechichi/ LinkedIn: https://www.linkedin.com/in/katechichi/
Chapters
0:00 Intro
0:51 Why tree care
5:08 Making the leap
10:02 Building the platform
23:09 The Northside deal
30:06 Private equity backing
38:33 Organic growth
41:54 A deal that nearly broke
48:03 The long game
55:24 How he uses AI
22 Sept 2026
How a Navy Vet Bought 4 Companies With Almost No Cash
Gary spent over 20 years operating nuclear reactors in the Navy. Now he owns a private equity firm and has bought four companies. He started with a Navy paycheck and one piece of advice.
Kate gets him to break down how he finds owners ready to sell, structures deals with almost none of his own cash, and turns separate companies into something worth far more together.
Inside the episode: the first deal that had 26 other buyers, the one question to ask before any acquisition, and the reverse merger that can double what a business is worth.
Gary
LinkedIn: https://www.linkedin.com/in/gmac00/ (https://www.linkedin.com/in/gmac00/)
Gary's Book: Set Your Own Goals or Someone Else Will (https://www.goodreads.com/book/show/223008239-set-your-own-goals-or-someone-else-will)
Deal Diaries with Kate
YouTube: https://www.youtube.com/@dealdiaries_katechichi (https://www.youtube.com/@dealdiaries_katechichi)
Spotify: https://open.spotify.com/show/033DZHytD6ER7B0qZ93TiC (https://open.spotify.com/show/033DZHytD6ER7B0qZ93TiC)
Instagram: https://www.instagram.com/dealdiaries_katechichi/ (https://www.instagram.com/dealdiaries_katechichi/)
LinkedIn: https://www.linkedin.com/in/katechichi/ (https://www.linkedin.com/in/katechichi/)
Chapters
0:00 Intro
1:09 Origin story of Gary
5:47 Starting in private equity
8:18 Finding deals
10:56 Funding deals
16:42 The first deal
25:15 Integrating companies
32:32 Built to sell
42:37 What are reverse mergers and why should you care?
46:31 Goals and leadership
8 Sept 2026
How to Buy a Biz for $0 Down
Most people spend their whole lives building one business. Lee Smith buys them, and he has done it 31 times.
In this episode of Deal Diaries, Kate sits down with Lee Smith, a UK business acquisition strategist who has spent 12 years buying, growing and selling companies across HVAC, renewable energy, roofing and construction. He owns seven businesses today and is on track for £100 million in revenue by 2028.
Lee Smith
Website: https://www.leeasmith.co.uk/ (https://www.leeasmith.co.uk/)
LinkedIn: https://www.linkedin.com/in/leeantonysmith/ (https://www.linkedin.com/in/leeantonysmith/)
Deal Diaries with Kate
Instagram: https://www.instagram.com/dealdiaries_katechichi/ (https://www.instagram.com/dealdiaries_katechichi/)
LinkedIn: https://www.linkedin.com/in/katechichi/ (https://www.linkedin.com/in/katechichi/)
Chapters
0:00 Intro
0:58 Why buy, not build
3:39 Surviving volatility
5:54 How to buy a company with no money down
8:48 Investor returns
10:37 M&A networks
12:00 Structuring a deal
17:34 A deal that failed
20:12 What he buys now
24:24 Why focus on revenue over EBITDA
26:39 Using AI
30:14 Ownership and control
34:12 Taking over gently
38:11 Advice for your first acquisition
40:43 Exit and letting go
25 Aug 2026
He Sold a $1.2M Company | Here's What He'd Do Differently
He built a $1.2M company. Then sold it — and realized he'd left money on the table.
Jefe Greenheart has filmed Matthew McConaughey, Tim Ferriss, and the families of 3 U.S. presidents. He won SXSW and NBA contracts and sold his business during the pandemic.
In this episode, Jefe Greenheart tells us exactly what he got wrong: selling without knowing what a multiple was, the team members he wishes he'd brought along, and how the deal could've been worth nearly double.
Plus how he's using AI to cut production costs without cutting his artists.
If you're thinking about selling a business one day, this one's full of lessons worth stealing.
Chapters:
0:00 Intro
5:04 The day SXSW and NBA both got canceled
10:48 "I didn't even know what a multiple was" - and why you should
14:52 "We can't let them know how valuable they are"
17:24 Imposter syndrome, self-worth, and owning your brag
24:40 His advice to sellers: don't do it in secret
27:49 Going from owner to employee (the part that stung)
29:35 Building his next company to sell from day one
34:59 "AI-enhanced, not AI-replaced": how he built the team
39:35 Winning clients with Claude + Loom (without the spam)
41:27 Scaling outreach while keeping the human touch
11 Aug 2026
How to Buy, Scale and Sell a Company (Why 90% of Deals Die in Diligence)
Most owners ask whether a goal is possible. Ajay Nwosu asks what would need to happen to make it a reality.
He bought a company, scaled and sold it. In this episode: why 90% of deals fail in diligence and how to get through it. Why he wouldn't stay on as an employee post-sale again. How to read culture before you buy a business. And how to get your valuation benchmarked.
Chapters
0:00 Intro
0:45 How he found an arbitrage business
2:07 Why culture is the oxygen — and how he measures it
4:47 How to know your multiple before you sell
6:08 Why velocity is the only moat
7:14 The question that changes what your team thinks is possible
9:25 How long a deal really takes (his took 9 months)
10:45 Why 90% of deals die in diligence
14:37 Half cash, half equity deal — and what is an earnout
16:30 Staying on after the sale: "if I could do it again, I wouldn't"
19:54 How he taught AI to be his thinking partner
23:27 Taking a sport to 156 countries and the Olympics
27:37 Nobody knows what they're sleeping on
Ajay Nwosu: linkedin.com/in/ajay-nwosu-99597992 (https://www.linkedin.com/in/ajay-nwosu-99597992/)
Kate Chichi: linkedin.com/in/katechichi (https://www.linkedin.com/in/katechichi/)
28 Jul 2026
How to Buy a Biz that Takes 15 hrs / Week (with Your 401k)
How an ER pediatrician in New York bought a marketing agency in Florida that only takes 15 hours a week to run — and financed it with his 401(k). Justin Hoskins shares how he did it all: the retirement-fund structure nobody talks about, why use a loan broker, and how he uses AI to spot red flags in the acquisition docs.
0:00 Intro
0:49 From ER pediatrician to acquisition entrepreneur
3:17 Why he passed on med spas
7:00 The spreadsheet with 27,000 businesses for sale
10:05 Finding an absentee business
15:07 The seller note that closed the valuation gap
17:29 Using your 401k to fund an acquisition (ROBS explained)
23:58 The attorney who gave him 25% odds of closing
25:15 Why use a loan broker
31:42 Earning employee trust as the outsider
37:29 The MSO play in the legal space
42:41 Using AI to spot red flags in acquisitions
13 Jul 2026
How to Buy $2M in Revenue Business While Working Full-Time
Connor Pera acquired a business in what most people would call a dying industry — and then doubled it from $2M to $4M with a second acquisition. In this episode, get his trick for getting sellers' attention and learn why passing on a "great" business like HVAC might be the best decision you ever make.
0:00 Intro
1:04 What separates searchers who actually close
2:37 The vending machine that changed his mindset
4:38 How to find a deal without quitting your job
12:14 Why he chose a "dying" industry over HVAC
19:45 Skipping SBA — and the earnout he's glad he got
24:35 The phone call that got him through closing week
27:46 Day one of running an acquired business
30:57 How he got sellers' attention (the unexpected channel)
37:09 Using AI to reverse-engineer a $100M blueprint
29 Jun 2026
From $300K Salary to $30M Valued Agency — How to Grow Through Acquisitions
Joey Mure walked away from $300K a year at Wells Fargo after discovering that banks secretly store more capital in life insurance than in real estate — and built a $30M-valued insurance agency off the back of that insight.
In this episode, Joey breaks down the 4x-buy, 15x-sell arbitrage that convinced him to start acquiring, the earnout clause that cost him real money when a lawyer changed the final draft, and why he ultimately walked away from a $150M roll-up plan in favor of a simpler path to nearly the same payout. Joey is the co-founder of Wealth Without Wall Street and has nearly 700 podcast episodes under his belt.
Subscribe for more real acquisition stories every week.
0:00 Intro
0:36 Introduction — Joey Mure
1:04 Why he left a $300K job at Wells Fargo
3:42 What is Infinite Banking?
4:42 How Wells Fargo secretly invests $19B in life insurance
9:34 What an insurance agency actually does
10:48 How a podcast accidentally became a global lead-magnet
15:55 How an insurance agency makes money (commissions, renewals & why it's sellable)
20:56 Why Joey decided to start acquiring companies
23:48 What Joey looked for in an acquisition target
25:12 How Joey found the businesses he acquired
27:13 From LOI to close: the 9-month diligence slog
29:50 The post-close mistakes he'd never repeat
36:53 How the deal was structured
40:20 How his insurance carrier financed the deal
42:13 Organic growth vs. roll-up: why he changed his mind
46:42 Investor DNA: how to find the right investment for YOU
51:04 Raising 5 kids to think like entrepreneurs
55:31 How Joey uses AI across the business
1:00:22 Guest recommendations
24 Jun 2026
Deal Diaries - Coming Soon!
Where owners share how they bought and sold businesses.
Launching June 30th!
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168 ratings
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