In many industries, top performers make other people far more money than they get to keep themselves. Think about professional athletes—millionaires playing for franchises owned by billionaires.

In other fields, the value a top salesperson drives for a brand is often only a fraction of what they earn in commissions. That’s because building and running the infrastructure of a company pulls them away from what they do best.

But what if that weren’t the case? What if someone offered all that infrastructure as a service, so you could become the brand, the owner, and your own boss?

That’s what Guy Gal, Co-Founder and CEO of Side, is building for real estate agents across the country. Side handles back-office operations and partners with agents on marketing with the explicit goal of empowering agents to build and own their own brands.

It may be the largest brokerage you’ve never heard of.

Guy discussed all of this with Camber Creek General Partner Jeffrey Berman and Head of Platform Lionel Foster.

1:53 A “$24 billion invisible brokerage”

3:05 Most productive agents already run businesses but do not own them, because brokerage infrastructure distracts from client service.

5:02 How Side collaborates with agents

8:07 Side’s unusually high gross margins

11:30 Why Side’s churn is so low

15:10 Guy says most brokerage-built marketing stacks serve the brokerage’s interests, not the agent’s.

18:15 Reducing agent workload and brokerage costs per transaction

23:40 Delivering same-day commissions

25:30 Guy shares stories of agents completing offers and amendments entirely from their phones while traveling.

26:05 Up next: voice-driven contract amendments and hands-free transaction management

29:05 Why agents working with Side are notoriously difficult for competitors to recruit

31:20 The two main reasons partners leave Side

36:27 Guy explains why Side should be valued as a technology company rather than a traditional brokerage

44:10 Managing customer acquisition costs in a highly fragmented real estate industry

48:00 Why Side chose sustainable growth during market contraction despite pressure to accelerate.

50:35 Jeffrey asks Guy to forecast the future of real estate brokerage over the next decade.

51:25 Guy argues the industry is structurally biased toward part-time agents and explains why that model is breaking down.

52:45 Guy outlines a future with fewer, more professional agents handling more transactions through apprenticeship-style pathways.

54:10 Guy explains how recent rule changes governing commissions may accelerate consolidation toward experienced professionals.

In this episode, we are going to do something extraordinary. We are going to demystify classical music with the help of a Grammy-winning maestro, because Catalyst listeners deserve only the best. James Blachly is an orchestra conductor.

He loves the three Bs: Bach, Beethoven, and Brahms. But he's winning acclaim for reintroducing the world to outstanding composers whose scores might literally disintegrate if not for the excavation work he and his collaborators perform. And he's making it okay to dance like a maniac to the Rite of Spring.

Any industry like classical music that is designed to consistently produce peak performance can feel imposing. Excellence requires a great deal of effort. But James reminds us that all that effort isn't worth anything unless it builds connections between people.

1:15 The surreal experience of winning a Grammy over Zoom

2:45 The M word

5:10 Elitism within classical music

6:00 James is proud to be a bridge into classical music and describes orchestral listening as one of the most profound shared human experiences.

11:30 What hearing a great orchestra in a great hall and attending a Major League Baseball game for the first time have in common

12:40 An orchestral performance is uniquely designed to produce peak human experiences on a regular basis

16:16 Jame’s upbringing. He did not grow up in a castle.

20:28 Experiential Orchestra lives up to its title

22:10 The Rite of Spring dance party

23:28 A lot of classical music was originally written as dance music, not for passive listening.

27:45 Imagining music from someone else’s ears

28:35 Historical concert practices differed dramatically from today’s expectations. There was food and conversation. Plus: the origin of the encore.

31:36 James’ Grammy-winning work expanding the classical canon.

39:05 Building and maintaining a career as an artist

41:00 Conductors get better with age.

43:53 How the Grammy changed James’ career

A 529 plan is one of the best financial tools that too few people are using. If you’ve heard of them, then you know they can help families save for children’s higher education. But did you know adults can use them too, that they can cover some K-12 expenses, study abroad, student loans, and support people with disabilities? These incredibly versatile accounts are, sadly, woefully underutilized. That’s in part because finding the best plan for your circumstances can be a pain.

In true entrepreneurial fashion, Yosh Miller set out to change this. His company Hadley wants to make 529s as ubiquitous as 401ks. But as you will hear, the bureaucracy and perverse incentives he has to navigate are astounding.

1:14 Lionel is a 529 plan geek.

3:09 529s might be one of the most powerful yet misunderstood tools in the US tax code.

3:40 Yosh compares 529 plans to Roth IRAs: tax-free growth and tax-free withdrawals with broader eligibility.

5:04 They’re not just a college savings plan.

7:00 Hadley’s origin story

8:25 Yosh explains how state-by-state rules create confusion and why many Americans should shop across states for better plans.

11:50 From solving a personal problem to recognizing a systemic, nationwide issue

14:20 Yosh highlights the shocking inequity in 529 adoption, noting that the wealthiest Americans dominate participation.

23:00 A newly minted entrepreneur navigates big administrative hurdles

27:05 For Hadley, going through employers is the most efficient go-to-market strategy.

34:20 Yosh shares his guiding principle of “finding the friend in the room” to drive systemic change.

35:19 Lionel explains how a LinkedIn post about 529s led to discovering Hadley and connecting with Yosh

37:20 A specific example of how Lionel uses 529s

40:40 Recent policy changes allowing 529 funds to roll into Roth IRAs

42:00 The gift that keeps giving: expansions of 529 benefits across multiple federal administrations

42:40 Early investor skepticism of Hadley