How Agencies Win Larger Deals to Scale

A podcast about how agency founders and senior operators build their go-to-market engine, test new growth channels, win larger deals, and scale.

Apply to join the show
Host responds within 48 hours.
90K+
Founders and executives
$10M–$150M
Avg. Guest Revenue
40+
Leaders featured
Featured Guests
Tom Shapiro Gilad Bechar Shoshana Winter Kathryn Wilson Stefanie Beach Fernando Cao Lori McDonald Will Harris
40+ founders and operators have shared their playbook
On the Show Tom Shapiro
On the Show
Tom Shapiro
Helped scale an agency from $12M to $75M in five years.
Joined by agency founders and operators from these companies:
Torro Media Elumynt Moburst Converge Marketing Stratabeat AdVenture
Recent guests

Agency leaders who've joined us

Tom Shapiro
Helped scale a business from $12M to $75M in 5 years
Guest Highlights
Speaker30+ engagements
ClientsIntel, GE, AT&T, UnitedHealthcare
WinMade $40M by mailing movie tickets
Gilad Bechar
Built a 100-person business through 5 acquisitions
Guest Highlights
Acquisitions5 in 6 years
ClientsGoogle, Uber, Samsung, Reddit
AITransformed agency to be AI-Native
Shoshana Winter
Led a 60-person turnaround out of bankruptcy
Guest Highlights
RoleCEO of Converge
Team86 people, 3 continents
Prior25 yrs Audible, Dentsu, Merkle
Kathryn Wilson
Built a 35-person pharma business
Guest Highlights
Brands24+ launched
Team35 FTE + 300 freelancers
ClientsNovo Nordisk, Apellis, Merz
Stefanie Beach
Manages $175M in ad spend across 62 brands
Guest Highlights
Growth763% in 3 years
Rankedon Inc. 5000
OriginBuilt post-layoff while raising her daughter
Lori McDonald
Ex-NASA built an agency that drove $750M
Guest Highlights
OriginEx-NASA Shuttle Flight Controller
Client impact$750M revenue added (2015-23)
RecognitionInc. 5000 (twice)
Will Harris
Drove 13 ecommerce exits. Biggest sold for $800M
Guest Highlights
Exits13 acquisitions
Biggest deal~$800M sale
ClientsNike, Nickelodeon, Jack Daniel's
Dr. Brent Ridge
Built a $150M skincare brand from Goat milk
Guest Highlights
Revenue$150M+ in sales
Team220+ employees
BackgroundHarvard-trained MD, ex-Martha Stewart VP
Tom Coburn
Raised $92M for his SaaS. CEO of the Waking Up Meditation app
Guest Highlights
Raised$92M for Jebbit
ClientsNFL, Pepsi, Bank of America, L'Oréal
NowCEO of Waking Up
This podcast is for you if you are...
The founder, CEO, or senior operator of an established agency
Close to the agency's go-to-market motion and involved in how the business acquires clients and grows
Willing to share specific experiments: what worked, what failed, and what you'd do differently
Who we're speaking with
Established leaders across marketing, creative, advertising, PR, development, recruiting, and consulting agencies
Operators experimenting with outbound, partnerships, referrals, events, content, paid acquisition, communities, acquisitions, and emerging channels
Agency leaders with real numbers, specific experiments, unexpected challenges, and lessons from serving mid-market and upmarket clients
About the show
This show is for agency leaders willing to share what is actually working (and what's not) as they build a stronger go-to-market engine and serve larger clients.

Every episode covers three things:

01
How you win businessYour positioning, ideal clients, offers, acquisition channels, sales motion, and how those have changed as the agency has grown.
02
The experiments that moved the agency forwardThe channels, partnerships, hires, technology, and GTM bets that produced larger or better-fit clients.
03
What you're experimenting with nowThe channel, sales, delivery, retention, or operating challenge you're working through as you serve larger clients.
Guests join to share their expertise and what they're experimenting with to grow their agency.
Recent content

Watch a recent episode

30–60 minute interviews with agency founders and operators.

Tom Shapiro Made $40M… Mailing Movie Tickets
Tom Shapiro Made $40M… Mailing Movie Tickets
39:36
Fernando Hit $350K a Month (All From Twitter)
Fernando Hit $350K a Month (All From Twitter)
1:01:53
She Rebuilt a 60-Person Agency (Steal Her Turnaround Playbook)
She Rebuilt a 60-Person Agency (Steal Her Turnaround Playbook)
54:15
Kathryn Wilson Built a 35-Person Agency (By Ignoring Profit)
Kathryn Wilson Built a 35-Person Agency (By Ignoring Profit)
28:48
Stefanie Beach Built a 7-Fig Agency (From Her Hospital Bed)
Stefanie Beach Built a 7-Fig Agency (From Her Hospital Bed)
24:08
How Blake Runs a 100-Person Agency (With Only 5 Full-Timers)
How Blake Runs a 100-Person Agency (With Only 5 Full-Timers)
37:12
Competitors Undercut Jason Fishman With AI (He Still Raised $100M)
Competitors Undercut Jason Fishman With AI (He Still Raised $100M)
31:46
He Built an Ad Network During COVID (Then Signed 10,000 Brands)
He Built an Ad Network During COVID (Then Signed 10,000 Brands)
59:25
He Expected 9/11 to End His Business (Then Made $1M In A Week)
He Expected 9/11 to End His Business (Then Made $1M In A Week)
24:16
Someone Gave Brent 100 Goats (Didn't Know They'd Make Him $150M)
Someone Gave Brent 100 Goats (Didn't Know They'd Make Him $150M)
38:10
Want your story to be next?
Apply to be a guest
From LinkedIn

Check us out on LinkedIn

Each episode becomes 3 LinkedIn posts.

Today you can start a business by lunch. Test it by dinner. And kill it before it costs you $9. Where's my team? 3 people had quit before Stephane started. He called it a godsend. Hiring stopped David's business from scaling. So he built a system (& scaled to 20 employees). Lori grew e-commerce demand so fast. She ran out of product. Here's what that did to her team. His agency had 50 employees and growing revenue. One question revealed 3 problems he'd ignored for years. A fix that costs $500 at $1M costs $50,000 at $5M. Here's how Kathryn makes sure it never gets this far.
Want your story to be next?
Apply to be a guest
Scaling topics we cover

Where we go deep

How established agencies find larger clients

The channels, positioning, and trust-building strategies creating qualified opportunities with larger companies.

  • Which acquisition channels are producing larger, better-fit clients
  • What changes when the buyer is larger and the deal is more complex
  • What experiments failed and what they'd skip next time
Building a repeatable agency GTM engine

How agency leaders move beyond founder-led referrals and build a growth motion that supports mid-market and upmarket accounts.

  • Positioning, specialization, offers, pricing, and sales process
  • Hiring and managing sales or growth leadership
  • Expanding, retaining, and delivering for larger client relationships
Our Mission

Lessons from the Agencies in Scale Mode

At a certain stage, generic agency advice stops being useful. What helps is stories. Stories from other agencies in the trenches.

Hearing exactly how another agency tested a channel, won a larger client, fixed a broken sales motion, or recovered from a bet that did not work.

Legends of Scale gives agency founders and operators a place to share those stories. The numbers, decisions, mistakes, and lessons they wish they had heard earlier.

No cost. Just agency leaders helping other agency leaders build stronger businesses.

Rising tides lift all ships.

Have an agency growth story worth sharing?
Apply to be a guest
The host

Meet your podcast host

Brian O'Connor, host of Legends of Scale
Brian O'Connor
Founder and host, Legends of Scale

I spent 6 years as a growth strategy consultant at Deloitte. Helped 35 of the biggest companies in the world solve their growth problems. I can't say exactly which but think companies like Coca Cola, Salesforce, Facebook and you won't be too far off.

Then I left. I wanted to help real founders, not Fortune 500s.

So I started posting the frameworks I'd been using at Deloitte. A few years later: 90,000+ founders and execs followed along.

Those same founders asked for support growing their business. So I built B2B Pods. We show people what an incredible podcast experience looks like. They experience how powerful it is to get free content that builds trust and relationships. When they're ready to build weekly relationships with their own mid-market clients, we build and run it for them.

Rising tides lift all ships.

I built the podcast I wish existed: nerdy business stories about how companies go to market.

How this works

What to expect

From applying to your episode going live.

01
You apply
Tell us about your agency, the clients you serve, your role in the GTM motion, and the growth experiment or lesson you want to share. We accept roughly one in four applicants based on fit with the season and variety for the audience.
02
We chat
A quick screening call to talk about your GTM motion, who you serve, and make sure it's a fit for the show.
03
We record
One hour. We talk about the unique aspects of your GTM motion and the experiments you're running.
04
We distribute
Your story becomes a long-form YouTube episode, short-form videos, and LinkedIn content.
Common questions

FAQ

Who's the right fit for the show?
Founders, CEOs, and senior operators at established marketing, creative, advertising, PR, development, recruiting, and consulting agencies. The best guests make scaling decisions, are close to GTM, and can speak honestly about channels, larger deals, and lessons learned.
How many people get accepted?
It depends on the season, but right now it's roughly one in four applicants. We curate for fit with the season's target clients and GTM focus, and to give the audience a useful variety of agency models and growth motions.
What will we discuss?
We talk about how your agency gets clients, which channels and experiments you've tested, what changed when serving larger companies, and the GTM challenge you're solving now.
Is this only for agency founders?
No. Senior operators can apply when they're directly involved in scaling decisions and close to the agency's GTM motion.
What happens after the episode airs?
The episode is posted across Spotify and Apple Podcasts, Instagram, YouTube, TikTok, and LinkedIn. You'll get a content calendar and a plan to share and distribute the content together. If you're wrestling with a constraint and someone in Brian's network can help, he'll make the connection.
What does it cost?
There is no cost. We've been creating content for five years and are motivated to give guests an amazing free experience while building relationships with the audience and guests. We build podcasts as a service, so when someone is ready to meet their mid-market dream clients more consistently, they think of us.

Have an agency growth story worth sharing?

Fill out the form and Brian will respond within 48 hours
Brian reviews applications personally. If you lead an established agency, are close to the GTM motion, and can share a specific lesson about winning and serving larger clients, we'd like to hear from you.
© 2026 Legends of Scale · A Brian O'Connor Podcast
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