Guest: Greg Moran – Multi-exit founder, investor, and Managing Partner at Evergreen Mountain Equity Partners
Host: Alex Rawlings, Founder of Raw Selection

⏱️ Timestamps & Topics

00:00 – Introduction to Greg Moran
Alex welcomes Greg Moran, a multi-exit founder turned investor, and Managing Partner at Evergreen Mountain Equity Partners. Greg introduces his background in scaling businesses, raising $500M+ in capital, and his current focus on future-of-work technologies.

01:29 – Biggest Mistakes in Private Equity & Venture
Greg highlights two major missteps:

1. Private Equity: Disrespecting existing leadership and stripping company culture.
2. Venture Capital: Failing to deeply understand a founder's motivations under pressure.

03:51 – Behavioral Due Diligence: The Adaptive Innovator
Greg explains how Evergreen Mountain uses a proprietary founder archetype model based on studying 100+ founders with multiple 9-figure exits.
📘 Book: The Adaptive Innovator
🔬 Assessment Tool: theadaptiveinnovator.ai

06:11 – The Four Pillars of the Adaptive Innovator Model

1. Creative Resilience – Performing better under pressure
2. Balanced Risk-Taking – Small experiments lead to bold moves
3. Humble Assertiveness – Leading without being the loudest voice
4. Strategic Accountability – Owning failures and empowering teams

09:09 – How the Assessment Works
Greg walks through the free assessment's design—competency-based and situational judgment questions that help reveal how founders respond under real pressure.

11:37 – From Operator to Investor: The Shift
Greg discusses the personal challenge of moving from "solver" to "sounding board" and helping founders overcome small thinking and incrementalism.

15:01 – Scaling Requires Talent Transformation
Once you think bigger, the next hurdle is team capability. Greg discusses the importance of upgrading talent and how average hires dilute culture and repel A-players.

18:26 – “Hire Fire and the Walking Dead”
Greg's framework on talent management:

• Hiring is easy
• Firing the clearly bad is manageable
• The real issue? Keeping the “walking dead” – the average, inoffensive underperformers who drain momentum.

20:21 – Coaching Founders Through Tough Talent Calls
Greg explains his approach as an investor: gently keeping the conversation alive, helping founders reach the inevitable realization themselves.
🗣️ Anecdote: The "5-second hesitation test" from a former board member.

31:27 – Recommended Reading & Interests
📖 The Alchemist by Paulo Coelho – a yearly re-read for Greg
🎒 Outdoor adventure and Alaska documentaries (his son is a bush pilot)

32:52 – How to Connect with Greg Moran

• 🌐 Website: gregmoran.me
• 🧠 Assessment: theadaptiveinnovator.ai
• 💼 Fund: emep.io
• 🔗 LinkedIn: Greg Moran
• 📺 YouTube & X (formerly Twitter): Active channels for the docuseries and insights

Raw Selection partners with Private Equity firms and their portfolio companies to secure exceptional executive talent. We focus on de-risking executive recruitment through meticulous search and selection processes, ensuring top-tier performance and long-term success.

🔗 Connect with Alex Rawlings on LinkedIn: https://www.linkedin.com/in/alexrawlings/
🌐 Visit Raw Selection: www.raw-selection.com

🕒 Episode Timestamps & Show Notes

00:00 – Introduction
Alex welcomes John Dwyer, Founder of The Institute of WOW, to explore how direct response marketing can drive real results for private equity firms and their portfolio companies.

00:53 – What is WOW Factor Marketing?
John explains his flipped model: get prospects to try your product so they fall in love with your brand—not the other way around.

02:16 – The Power of Incentives
Examples like McDonald’s Happy Meals and Kellogg’s cereal toys demonstrate how incentives remove focus from price. Yet, 97% of businesses still fail to use them effectively.

03:35 – B2B Application of Incentives
John shares how “freemium” strategies—like webinars and educational content—can help service businesses generate leads and build trust.

05:25 – The PE Blind Spot: Marketing
Marketing is often underutilized at the PE firm level. It’s left to portfolio companies and only becomes a priority at scale ($100M+ revenue).

06:21 – Creating High-Value Content
Instead of always documenting, John recommends delivering structured, high-impact content like digital resources to demonstrate expertise and create authority.

08:36 – Giving Away IP to Build Trust
Sharing ideas freely (within reason) helps firms position themselves as experts. Private equity firms can do the same by publishing their value creation playbooks.

09:33 – Case Study: Dental Facebook Contest
A $30/day contest targeting parents of kids with crooked teeth generated 1,000+ leads in a week—demonstrating the power of a well-crafted incentive-based campaign.

12:43 – PE Deal Origination via Events
John recommends PE firms host webinars or in-person events to share their expertise and attract business owners—selling “once to many” like Tony Robbins.

14:11 – Thinking Beyond Traditional Marketing
John suggests PE firms partner with data providers or influencers to host educational events. Joint ventures and revenue-share models can scale reach efficiently.

17:27 – Turnkey Marketing & Strategic Partnerships
From travel vouchers to million-dollar contest giveaways, John shares how creative incentives combined with strong partnerships can produce scalable campaigns.

19:10 – Using AI for Lead Generation
John discusses how AI-powered voice bots deliver high-volume outreach, sharing relevant data like estimated home values—ideas that can inspire new B2B tactics.

21:57 – Hiring Great Marketers
John stresses the importance of case studies and results over resumes. Look for marketers who can think outside the box and prove success with real-world campaigns.

24:21 – Purple Cow Thinking in Action
A standout example: A building society offered free holidays for mortgage customers and later added Jerry Seinfeld to the campaign—resulting in billions in new loans.

26:42 – Books & Resources
John recommends The Purple Cow by Seth Godin. He prefers audio content and real-world business insights over fiction.

28:04 – How to Contact John
📩 Email: john@theinstituteofwow.com
🌐 Website: theinstituteofwow.com

Raw Selection partners with Private Equity firms and their portfolio companies to secure exceptional executive talent.
We focus on de-risking executive recruitment through meticulous search and selection processes, ensuring top-tier performance and long-term success.

🔗 Connect with Alex Rawlings on LinkedIn: https://www.linkedin.com/in/alexrawlings/
🌐 Visit Raw Selection: www.raw-selection.com

Episode Summary:
In this insightful episode, Alex Rawlings is joined by Brett Hickey, the CEO and founder of Star Mountain Capital. Brett shares his unique journey from humble beginnings in Northwestern Canada to leading a multi-billion-dollar asset management firm in the U.S. With deep reflections on leadership, value-based investing, building collaborative ecosystems, and what truly drives sustainable success in private markets, this is a masterclass in private equity thinking.

Brett also discusses the strategic opportunities in the U.S. lower middle market, the implications of aging demographics, his risk-aligned investment strategy, and the power of culture in scaling a firm. If you're looking to understand how to build a high-performing investment organization from the ground up—and what books, frameworks, and philosophies support that—this episode is essential listening.

⏱️ Episode Highlights & Time Stamps:

00:00 – Welcome and Introduction to Brett Hickey
00:41 – Overview of Star Mountain Capital and its focus on U.S. lower-middle market private credit, secondaries, and private equity
01:12 – Key mistake PE firms make: passive asset management vs. active value creation
03:08 – Aging demographics as a key investment opportunity
04:05 – Valuation arbitrage in lower middle market businesses
05:05 – Reflections on a possible downturn: macroeconomic risks and “air pockets”
07:59 – Aging populations and structural economic concerns
09:53 – The importance of cash flow and capital protection
10:21 – Brett’s entrepreneurial journey – from launching his first fund at 26 to building Star Mountain Capital
12:41 – The S-shaped growth curve and persistence through innovation
13:40 – Brett’s data-driven approach to strategy and decision making
15:35 – Why aging demographics and inefficient markets create opportunity
17:08 – Biggest challenge in building the firm: People
19:30 – Aligning team culture and expectations through transparency and shared values
20:57 – Why Star Mountain is 100% employee-owned – benefits and challenges
22:54 – Building trust and long-term alignment through ownership
24:45 – Observations on asset management failures and strategic missteps
25:44 – What is the Collaborative Ecosystem and how it drives results at Star Mountain
27:34 – How peer networks like EO and YPO influenced the firm’s internal culture
28:31 – Leveraging insights between secondaries and direct investments
29:59 – Case studies, adjusted EBITDA, and forensic underwriting
31:18 – Using real business alignment as a differentiator in competitive deal processes
33:13 – Recommended reading: Brett’s top books and content on leadership and execution
33:41 – Never Lead Alone by Keith Ferrazzi
34:37 – Agility by Leo Tilman and General Chuck Jacoby
36:54 – Harvard Business Review and Rob Kaplan’s work on leadership
38:48 – Principles by Ray Dalio and how it influences Brett’s thinking
39:18 – A practical tip: triangulating decisions with deep experts
41:13 – Final reflections on value investing, risk management, and staying grounded
42:09 – How to get in touch with Brett and Star Mountain Capital
42:38 – Wrap-up and takeaways from Alex

🔗 Connect with Alex Rawlings on LinkedIn: https://www.linkedin.com/in/alexrawlings/
🌐 Visit Raw Selection: www.raw-selection.com