Brian O'Connor

Legends of Scale

Business EN ↓ 27 episodes

In this show 7 - 8 figure founders share the truth of how they scaled their business. The business model. What they tried (and didn't work). And the scaling tricks they use to grow: SOPs? Hiring? AI?We're joined by digital service business owners: agencies, coaches, and consultancies.

Author

Brian O'Connor

Episodes

Adam Connors Had 0 Fancy Degrees (But Won Deals Harvards Couldn't) 02.07.2026 1:08:20

Today we talk with Adam Connors, founder of Network Wise. 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor --- 0:00 Meet Adam Connors 1:10 Wall Street to Hedge Funds: Adam's Wild Career 4:00 No Pedigree, But Harvard Grads Couldn't Compete 8:18 Network Mapping: Find Anyone Strategically 10:18 Trust Is...

Michael Kleinmann Saved an Ecomm Client $40k (Uncovering ONE Common Mistake) 01.06.2026 52:07

Today we talk with Michael Kleinmann, founder of Underwear Expert and Ecomm consultant. 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor --- 0:00 Meet Michael Kleinmann 1:32 FreshPair to Subscription: The Pivot 3:15 Building an Audience Before Selling Anything 5:55 Why Subscription Forces You to Nich...

Fernando Cao Hit $350K a Month (All From Twitter) 20.05.2026 1:01:54

Today we talk with Fernando Cao, founder of RevenueFlow. 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor --- 0:00 Meet Fernando Cao 0:30 From Personal Brand Agency to a $3M GTM Agency 2:08 Hiring 50 People in 4 Months "Sounded Sexy on Paper" 6:31 The Centralized Intelligence System Powering His Agen...

Stefanie Beach Built a 7-Fig Agency (From Her Hospital Bed) 20.05.2026 24:09

Today we talk with Stefanie Beach, founder of The Marketeer Group. Find Stefanie here: www.themarketeergroup.com https://open.spotify.com/show/2ciqhrDOYoow1OIKswNVXk https://www.youtube.com/@TheDigitalMarketeerPodcast 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor 0:00 Meet Stefanie Beach 0:30 Laid...

Will Harris Lost His Nursing Job in 2008 (Didn't Know He'd Build $800M Exits) 20.05.2026 36:39

Today we talk with William Harris, founder of Elumynt. 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor Chapters 0:00 Meet William Harris 1:06 The Accidental Agency Origin 4:24 Hiring a Partner 3 Days Before COVID 5:22 Why Employees Beat Contractors at Scale 9:31 Remote Culture Built From Day One 17:...

Someone Gave Brent Ridge 100 Goats (Didn't Know They'd Make Him $150M) 20.05.2026 38:11

Today we talk with Brent Ridge, founder of Beekman 1802. 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor Chapters 0:00 Meet Brent Ridge 1:25 The Target Deal That Almost Bankrupted Beekman 4:21 Why Big Brands Stock Their Own Shelves 6:52 "We Wouldn't Spend a Dollar Until We Made $1.50" 13:22 "We Neve...

Competitors Undercut Jason Fishman With AI (He Still Raised $100M) 20.05.2026 31:46

Today we talk with Jason Fishman, founder of Digital Niche Agency (DNA). 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor --- 0:00 Meet Jason Fishman 0:17 75 Pitch Decks to Raise $3M 1:10 Why He Built DNA in 2014 3:06 The Rule Change That Opened Investor Ads 4:49 From Basic Ads to Full-Funnel Investor...

Joshua Iverson Sold the First Facebook Ads (Now Manages $200M in Ad Spend) 20.05.2026 39:08

Today we talk with Josh Iverson, founder of iMediaAudiences. 💼 Join 47,000+ following on LinkedIn: http://www.linkedin.com/in/brianfoconnor 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor --- 0:00 Meet Joshua Iverson 0:22 Selling the first ads on Facebook 1:12 The first scale moment 1:44 Losing $100K/month overnight 2:54 Building a genealogy ad network 3:54 First internal hire a...

Lori McDonald Went From NASA Engineer to 20-Person Agency Founder 20.05.2026 47:23

Today we talk with Lori McDonald, founder of Brilliance Business Solutions. A 20-person ecomm marketing agency. 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor --- 00:00 We Sold Out — Then Hit a Wall 00:19 NASA to Founder: Lori’s Unlikely Career Pivot 00:49 The Brutal “Hobby vs Business” Moment 04:1...

Lior Eldan Saw AI As An Existential Crisis (Now It Runs The Agency) 20.05.2026 38:56

Today we talk with Lior Eldan, co-founder and COO of Moburst. 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor --- 00:00 Meet Lior Eldan 00:20 From a Kitchen in Israel to Google and Samsung 00:58 "We Kind of Stumbled Into Being an Agency" 02:44 The Moment AI Felt Like an Existential Threat 05:42 Why...

Stephane Gringer's Team Quit on Day 1 (He Called It a Godsend) 20.05.2026 35:36

Today we talk with Stephane Gringer, founder of Voxaic.ai 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor --- 0:00 Meet Stephane Gringer 1:10 When Brand Owners Couldn't Tell It Was AI 2:14 The 1,000-Ad Problem Nobody Talks About 4:08 How to Know When Your Brand Is Drifting 8:27 "People Buy With Emot...

Jason Berkowitz Learned SEO to Get Gym Clients (Then Built a 7-fig Agency By Accident) 20.05.2026 44:26

Today we talk with Jason Berkowitz, founder of Break the Web. 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor ---- 00:00 Meet Jason Berkowitz 01:12 The Exit Interview That Forced Him to Delegate 02:33 Building Links From His Queens Apartment 05:39 Why He Went Fully Global (Zero US Employees) 10:02 "...

Kathryn Wilson Built a 35-Person Agency (By Ignoring Profit) 20.05.2026 28:49

Today we talk with Kathryn Wilson, Founder and CEO of VUE Health. --- 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor 00:00 Meet Kathryn Wilson 00:56 She Built an Agency From Scratch — Senior First 03:08 Why Most Founders Hire Too Late and Too Junior 03:20 "Lack of Leadership Is Expensive" 04:10 How...

David Reske Built a 50-Person Agency (Then Sold It to Start From Zero) 20.05.2026 36:04

Today we talk with David Reske, founder and CEO of Nowspeed. --- 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor 00:00 Meet David Reske 01:11 The Moment Nowspeed Became Real 02:39 Why Founders Can't Build Sales Teams 04:30 The 3 Things That Fixed Sales 07:15 "The Number One Thing: Stop Hiring" 09:28...

Nate McKelvey Expected 9/11 to End His Business (Then Made $1M In A Week) 20.05.2026 24:17

Today we talk with Nate McKelvey, founder and CEO of Bobos AI. --- 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor 00:00 Meet Nate McKelvey 01:06 Building Jets.com Before Google Existed 04:05 "I Maxed Every Credit Card I Had — and My Wife's" 04:55 Growing Too Fast (It Set Them Back a Full Year) 05:5...

Alessandro Bogliari Bet His Last $1,500 on TikTok (Now Runs a 50-Person Agency) 20.05.2026 44:01

Today we talk with Alessandro Bogliari, co-founder and CEO of The Influencer Marketing Factory. --- 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor 0:00 Meet Alessandro Bogliari 0:11 From $1,500 to Google, Sony & Hyundai 0:52 The Moment He Couldn't Do It All Alone 4:13 Why Finance Was So Painful...

How Blake Minho Kim Runs a 100-Person Agency (With Only 5 Full-Timers) 20.05.2026 37:13

Today we talk with Blake Minho Kim, co-founder of Myosin, a marketing network helping web3 companies grow. --- 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor 0:00 Meet Blake Kim 0:44 "A Traditional Agency Is a Ponzi Scheme" 1:04 Why the Agency Model Is Broken 6:13 What Members Get Instead of a Sala...

Shoshana Winter Rebuilt a 60-Person Agency (Steal Her Turnaround Playbook) 20.05.2026 54:16

Today we talk with Shoshana Winter. The second employee at the world's first social network, now CEO of Converge Marketing. --- 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor 00:00 Intro 00:29 What She Walked Into 02:32 Why Clients Were Shaky 05:13 Fixing At-Risk Clients 07:08 Rating Every Client 1...

Patrick Gilbert Refused AI for 3 Years (Today He's Google's AI Speaker) 20.05.2026 1:43:22

Today we chat with Patrick Gilbert. CEO of AdVenture Media. --- 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor 00:00 Intro — Meet Patrick Gilbert 01:17 How Patrick Went From AI Hater to AI Superfan 04:41 Doubling Every Year — Then Hitting the Wall 08:06 What Structure Did He Cut (and Why)? 10:06 Bu...

Adrian Fagerlund Built an Ad Network During COVID (Then Signed 10,000 Brands) 20.05.2026 59:26

Today we chat with Adrian Fagerlund. Founder and CEO of Linkby. --- 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor 00:00 Meet Adrian Fagerlund 00:15 Launching a marketplace during COVID 00:57 The chicken-or-egg problem, getting the first brands and publishers 2:31 "We had to hire 15 people at once"...

How Sam Schmitt's SaaS Got 70,000 Users (W/o Quitting His Day Job) 20.05.2026 36:31

Today we chat with Samuel Schmitt. Founder of Thruuu — an SEO tool used by 70,000 people. --- 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor 00:00 Meet Samuel Schmitt 00:18 Building an SEO tool with zero SEO knowledge 00:59 Why he kept the tool completely free for 2 years 05:07 Losing 3 years of gr...

Gilad Bechar Cut Costs With AI (But Hired Like Crazy) 20.05.2026 41:24

Today we chat with Gilad Bechar Founder of Moburst. --- 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor 0:00 Meet Gilad Bechar 0:11 All-In on AI (But Hiring More, Not Less) 0:48 "We Thought We'd Downsize" 3:32 The Roles Nobody Expected to Create 6:48 Why Every AI Tool Needs a Product Manager 8:17 Th...

Tom Coburn Quit Pre-Med (To Raise $92M) - #05 20.05.2026 40:22

Today we chat with Tom Coburn. Founder of Jebbit. CEO of Waking Up: A meditation app he's building with Sam Harris. --- 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor 00:00 Meet Tom Coburn 00:54 7 years of "fake" product-market fit 03:10 Winning a business plan with no code and dropping out of pre-...

A Lawsuit Drained Kevin Roy's Bank... Then He Built A 7-Fig SEO Empire - #04 20.05.2026 34:12

Today we chat with Kevin Roy. Founder and CEO of Green Banana SEO. --- 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor 0:00 Meet Kevin Roy 0:18 Starting from Craigslist (The Early Days of Green Banana) 1:55 The "Favorite Rock Band" Hiring Filter 3:20 The One Trait Kevin Refuses to Hire Without 4:50...

How Matt Sullivan Built a 7-Fig Marketing Agency (by Accident) - #03 20.05.2026 1:09:44

Today we chat with Matt Sullivan. Founder and CEO of Torro Media. --- 💼 Join 47,000+ following on LinkedIn: https://www.linkedin.com/in/brianfoconnor/ 🐦 Join 40,000+ following on Twitter: https://x.com/BrianFOConnor 0:00 Meet Matt Sullivan 0:45 The "Oh Shit" moment, "I can't do this alone" 2:07 Why hiring generalists was a mistake 7:10 "We were the guinea pig" testing on yourself before selling...