Acquiring Minds – Episode Summary

Episode Overview

Title: How to Build a $5m Media Business Into a $20m Flywheel
Date: November 6, 2025
Host: Will Smith
Guest: Clayton Collins (CEO, HousingWire)

This compelling episode dives into Clayton Collins’ journey of acquiring and transforming HousingWire—a B2B publisher for the housing industry—growing it from a $4 million digital media company to an ecosystem nearing $20 million. The conversation explores Clayton’s background, his entrepreneurial vision, strategies for growth through acquisition, the evolution of HousingWire's business model, and practical advice for those considering similar paths in media or acquisition entrepreneurship.

Main Discussion Highlights

1. Clayton’s Path to Acquisition (04:43–08:19)

• Background: Clayton started in banking at Citigroup, shifted into investment banking at RBC, where exposure to small media M&A deals sparked his entrepreneurial interest.
• Search Fund Catalyst: Learned about search funds at Duke, but decided to gain more experience first.
  • Quote:
    “I learned about search funds in business school in 2011... but felt like I wanted some more transactional experience and just exposure to the deal world before jumping down this path.” – Clayton Collins (06:26)
• Key Skillset: Early career team management at Citi in NYC prepared him most for running businesses; M&A skills shaped his acquisition orientation but management was more crucial.

2. The Search Fund and Acquiring HousingWire (12:47–17:56)

• Search Strategy: Focused on information services/data in real estate and finance.
• Finding the Deal: Serendipity and networking played a huge role—the deal surfaced through a connection at a Duke alumni event, not just cold outreach.
  • Quote:
    “Trade publications are an incredibly smart deal sourcing tool for searchers.” – Clayton (15:04)
• Traditional Search Approach: Funded by a diverse group of search fund investors, highlight on the importance of capital source diversity for flexibility and conviction.

3. Early Days at HousingWire (25:12–34:44)

• Original State: Digital B2B publication, 14 employees, $4M revenue (20% growth, strong brand loyalty).
• Revenue Model: Dominated by digital and print ad sales (10-15% print), early signs of content marketing.
• Margins: High (near 40% EBITDA), but unsustainable for scaling; Clayton rebalanced toward growth investment.
  • Quote:
    “Buying at nearly a 40% EBITDA margin... we could have stayed there but we would have stayed at that same size forever.” – Clayton (33:02)
• Vision: From the start, aimed to transform it into a ‘Bloomberg of housing’—integrating media, data, and events.

4. Strategic Vision vs. Investor Alignment (44:11–49:03)

• Entrepreneurship vs. Financial Engineering: Clayton intentionally opted for entrepreneurship through acquisition, not just cash flow optimization or ‘financial engineering.’
  • Quote:
    "Search is about helping aspiring entrepreneurs find a starting point and get into operations and lead a team... this path is about entrepreneurship, it's about leadership, it's about general management." – Clayton (44:11)
• Investor Buy-in: Not all investors bought into the big vision; about 60% participated in the acquisition.
  • Quote:
    “That is a reason we build diversified investor groups. Every deal is not going to be the right fit for every investor.” – Clayton (46:37)
• Key Learning: Capital diversity enables visionary strategies; investors with different backgrounds offer important flexibility.

5. Executing the Transformation: Key Moves (49:22–63:08)

Early Operational Challenges

• Sales Transition: Replacing the founder-led sales approach proved more difficult than expected; account execs relied heavily on founder’s direct pipeline efforts.
• Key Hire: First major move was hiring a head of sales, rebuilding a scalable, process-driven sales org.
  • Quote:
    “Building a sales org in those first few years was my number one challenge and got nearly all of our energy.” – Clayton (50:15)

Product and Acquisition Expansion

• New Revenue Lines: Newsletters, events, and later data/SaaS subscriptions.
• First Acquisition (2020): RealTrends (data + event), pivotal in expanding into real estate brokerage data/events.
  • Quote:
    "That [RealTrends] experience that we kind of acquired into the organization changed the face of how we do events... elevated our strategy to serving executive audiences." – Clayton (54:00)
• Events as Flywheel: Events not just for margin but as audience/community linchpin and source of editorial/ad relationships.
• Data Acquisition (2022): Altos Research—massive coverage of real estate listings, provided SaaS and data licensing; acquisition also leveled up HousingWire’s engineering/product DNA.

6. The Flywheel Model & Revenue Streams (58:50–75:18)

The Flywheel

• Tightly Integrated Ecosystem: Users move between news, newsletters, podcasts, events, and SaaS products in a non-linear, mutually reinforcing cycle.
  • Quote:
    “We don't think of the audience in a funnel. We think of it in a flywheel... people move through our business, experiment with the different products we have, and hopefully share content.” – Clayton (58:50)
• Content & Data Synergy: Editors/analysts cross-pollinate media, events, and data products, raising credibility and community loyalty.
• Leadership Focus: Each revenue stream (media, events, subscription/data) gets weekly attention from the leadership team.

Financial Outcomes

• Revenue Today: Projected close to $20M for 2025 (4–5x growth since acquisition, a mixture of organic and M&A).
  • Quote:
    “We’ll finish this year between 4, 4 and 5x where we started at $4 million... both organic and through M&A.” – Clayton (75:18)
• Valuation Levers: Focus on high-quality, recurring revenue (SaaS, data subscriptions) and scale through integration and M&A.

Notable Industry and Media Business Insights

What Makes B2B Media Work? (77:36–85:53)

• Event & Data Opportunities: Events strengthen customer bonds, feedback, and NPS—media companies with event and data legs are more resilient and profitable.
• Transitioning Print to Digital:
  • Not trivial; changing out legacy teams, retraining, or even full personnel swaps is often required.
  • Legacy brand value can help, but timeline and capital needs are significant.
  • Quote:
    “To take a traditional print publishing brand to a scaled digital audience... the team probably needs to change out 100%.” – Clayton (78:02)
• Industry Selection: True upside lies in industries with:
  • High regulatory involvement (consistent change and information needs)
  • High capital intensity (big ad budgets for big-ticket products/services)
  • Examples include: housing, logistics, healthcare, manufacturing.
  • Quote:
    “If there's high regulatory involvement, that means change is going to be frequent and news/information about regulation... becomes really important.” – Clayton (83:48)
• Beware Niche Traps: Some verticals simply aren’t large enough to scale beyond a small business, regardless of brand reach.

Memorable Quotes & Moments

• On Vision and Differentiation:
  “My vision for HousingWire was to be the Bloomberg of housing... a media and information services business serving housing professionals.” – Clayton (25:12)
• On Team Building:
  “As a CEO, the most important part of the job is hiring people with strengths other than yours to, to be around you.” – Clayton (10:45)
• On Direct Sales Relationships:
  “We have always maintained direct relationships with all our advertisers... some accounts we've been working with at this point for 20 years.” – Clayton (36:50)
• On Buying with Vision:
  “Search is about helping aspiring entrepreneurs... This path is about entrepreneurship, leadership, general management... only the best operators get to a point where they can really start thinking about using their business and its cash flows for their investments.” – Clayton (44:11)
• On Integration and Synergy:
  “All of the pieces flow together organically... the sum of the parts is definitely more valuable than the pieces, and the integration is how it all works.” – Clayton (61:29)

Timestamps for Key Segments

• 04:43 – Clayton’s career path & spark for entrepreneurship
• 12:47 – Search process & finding HousingWire
• 17:56 – Traditional search fund fundraising & capital diversity
• 25:12 – What HousingWire was at acquisition
• 33:02 – Margin profile and investment for growth
• 44:11 – Vision, entrepreneurship vs. financial engineering
• 49:22 – The early challenges: sales leadership & team rebuilding
• 54:00 – Acquiring RealTrends and transforming HousingWire’s event model
• 58:50 – The media flywheel and business model integration
• 65:00 – Events as product suite vs. integral community strategy
• 68:19 – Building the data business (Altos acquisition)
• 75:18 – Revenue growth and scale today
• 77:36 – Media opportunities, print-to-digital transitions, and market selection
• 83:48 – The biggest B2B media success levers: regulatory and capital intensity
• 85:53 – Podcasting as relationship engine and content discipline

Final Thoughts

• HousingWire and Clayton’s growth arc illustrate the power of visionary entrepreneurship in the acquisition world—where buying a business is just the start, not the end.
• Buyers should look for industries where informative media/data is necessary—think about regulation and big-ticket sales.
• Building a multi-pronged, integrated business model (media, events, SaaS/data) offers compounding advantages but requires real operational leadership, not just deal-making skills.

END OF SUMMARY

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