In this episode of The Private Equity Podcast, Alex Rawlings speaks with Zachary Darrow, Chief Executive of Darrow Everett and leader of the firm’s Private Equity and Securities Practice Group.

Zachary shares how Darrow Everett grew from a real estate and finance boutique into a full-service law firm with eight offices across the East Coast. He explains how the firm navigated the global financial crisis, the pandemic, client losses and changing interest rates by diversifying its services and pursuing strategic acquisitions and team lift-outs.

The conversation explores why integration is often the hardest part of professional-services acquisitions and how treating employees as a second group of clients can improve talent attraction, retention and performance.

Zachary also discusses Darrow Everett’s data-led approach to business development, including measuring conference ROI, producing targeted digital content and ensuring marketing activity reaches genuine decision-makers.

Alex and Zachary examine the growing intersection between private equity and legal services. They discuss the regulatory barriers to outside investment in law firms, the potential role of managed service organisations and how private equity could provide the capital and operational expertise required to modernise the sector.

Finally, Zachary explains how Darrow Everett is adopting AI. Current use cases include reviewing large volumes of litigation data, identifying potential omissions in legal documents and improving internal workflows—while maintaining human oversight and professional accountability.

Key Takeaways

• Build professional-services firms as businesses, not simply collections of practitioners.
• Successful acquisitions depend on fast, thoughtful cultural and operational integration.
• Founders should prepare their infrastructure, legal documentation and financial reporting before pursuing investment or an exit.
• Marketing activity should be assessed through measurable returns rather than tradition.
• AI can enhance legal analysis and productivity, but its output must still be checked by experienced professionals.
• Private equity could unlock significant growth within legal services if regulatory and ethical concerns are properly managed.

Timestamps

00:00 – Introduction to Zachary Darrow
01:00 – Building a business that happens to be a law firm
01:31 – Navigating the global financial crisis
02:28 – Diversification, marketing and acquisitions
03:25 – Lessons from team lift-outs and firm acquisitions
04:49 – Acquiring people-centric professional-services businesses
05:12 – Treating employees as a second client group
07:01 – Modernising legal-sector business development
07:58 – Measuring conference and sponsorship ROI
08:55 – Content-led digital marketing
11:48 – Lessons from advising founders and investors
12:01 – Why founders must prepare earlier
13:57 – “Make-ready” work before raising or selling
14:56 – Chief Outsiders
16:22 – Private equity’s opportunity in legal services
17:20 – Alternative business structures and MSOs
18:18 – Solving law firms’ capital constraints
20:17 – AI investment and transformation
21:15 – Darrow Everett’s adoption of legal AI
24:01 – AI use case: reviewing large datasets
25:29 – AI use case: strengthening legal documents
27:24 – Zachary’s recommended reading
28:22 – How to contact Zachary Darrow

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

In this episode of The Private Equity Podcast, Alex Rawlings speaks with Bill Bell, Fractional Chief Revenue Officer at Chief Outsiders, about building a repeatable sales engine that drives organic growth across private equity portfolio companies.

Bill explains why commercial due diligence is often far less rigorous than financial, legal, and operational diligence—and how this leads firms to underwrite ambitious growth plans against sales organisations that were never designed to deliver them. He shares why hiring more salespeople rarely fixes a broken system, what strong sales leadership looks like, and how documented processes, CRM governance, pipeline discipline, and structured onboarding create scalable performance.

The conversation also explores the risks of hiring competitors solely for their “black book”, the value of stage-gated sales processes in long-cycle industrial markets, and Bill’s experience growing a PE-backed North American business from $180 million to $325 million in revenue while more than doubling its EBIT margin.

Key Takeaways

• Diagnose the commercial engine before adding sales headcount.
• Assess whether sales managers are truly managing, coaching, and forecasting—not simply carrying major accounts.
• Build systems that make capable salespeople productive rather than relying on individual heroics.
• Use clear stage gates to qualify opportunities early and avoid wasting months on deals that will never close.
• Professionalising the leadership team and commercial function can unlock organic growth and support M&A integration.

Timestamps

00:00 – Introduction to Bill Bell and Chief Outsiders
00:52 – The biggest commercial mistake private equity firms make
02:17 – Why hiring more salespeople can increase cost, not revenue
02:46 – Diagnose, fix the infrastructure, then add capacity
03:17 – Four areas of commercial maturity to assess
04:46 – What makes an effective sales manager
07:03 – How manufacturing companies typically hire sales talent
08:00 – The danger of relying on a salesperson’s “black book”
08:56 – Building a sales system instead of hiring your way to growth
09:56 – Four foundations to establish before recruiting sales reps
11:24 – What a documented sales process should look like
11:53 – Using stage gates in an 18-month industrial sales cycle
13:43 – The hidden cost of pursuing customers who will not buy
15:40 – Bill’s biggest PE-backed growth success story
17:34 – Recommended books, masterclasses, and podcasts
18:58 – How to contact Bill
19:27 – Closing remarks

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

In this episode of The Private Equity Podcast, Alex Rawlings speaks with Bobby Ocampo and Sheldon Lewis, co-founders and managing partners of Blueprint Equity.

Following the successful close of Blueprint Equity’s $333 million third fund, Bobby and Sheldon explain how the firm identifies and supports high-growth B2B software companies. They discuss Blueprint’s early growth investment strategy, its direct sourcing infrastructure and the role its six-person operations team plays in supporting portfolio companies.

The conversation also explores the impact of artificial intelligence on software valuations, underwriting and value creation. Bobby and Sheldon explain how Blueprint has integrated multiple AI tools across sourcing, deal evaluation, portfolio operations and internal workflows.

They also share why vertical software businesses with deeply embedded customer workflows may be better positioned to withstand AI disruption than lightweight horizontal software products.

Key Topics

• Blueprint Equity’s early growth investment strategy
• Raising a $333 million third fund
• Investing in B2B vertical software businesses
• Building a large direct sourcing function
• Supporting founders with recruiting, go-to-market and RevOps
• Using AI to identify, prioritise and track investment opportunities
• Connecting multiple AI tools through an integrated technology stack
• Underwriting software businesses in an uncertain market
• Assessing founders in minority growth investments
• Moving quickly without creating employee burnout

Timestamps

00:00 Introduction
00:28 Blueprint Equity and the successful Fund III raise
00:53 The firm’s early growth equity investment thesis
01:43 Building the team and operations function
02:50 Common mistakes made by investment firms
04:21 Underwriting software businesses in the AI era
06:33 How Blueprint structures its value creation team
07:41 Recruiting and institutionalising portfolio companies
08:35 RevOps, reporting and financial visibility
09:53 How Blueprint uses AI internally
10:37 AI-driven sourcing and opportunity prioritisation
11:06 Using proprietary data in underwriting
12:32 Blueprint’s AI technology stack
14:01 Building a genuine direct sourcing strategy
15:24 The resources required for proprietary origination
16:46 Less obvious investment signals
17:14 Assessing the entrepreneur behind the business
18:13 Vertical software and the threat of AI disruption
20:25 Creating a fast-moving culture without burnout
22:09 Recommended private equity news and content
23:34 How to connect with Blueprint Equity

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

In this episode of The Private Equity Podcast, Alex Rawlings speaks with Paul Isaac, Managing Partner of Isaac Management LLC, about investing in lower-middle-market businesses through a permanent-capital model.

Paul explains why Isaac Management operates without a traditional fund, predetermined exits or outside investor pressure. He discusses the risks of overleveraging, the importance of understanding a company’s community and culture, and why higher interest rates have created a disconnect between buyer expectations and seller valuations.

The conversation also explores Paul’s journey from banking and private credit to launching his own investment firm, how buyers can build trust with founders, and why operational improvement and talent development often create more sustainable value than financial engineering or acquisition-led growth.

Key Takeaways

• Why excessive leverage and weak market understanding can undermine an acquisition.
• How permanent capital supports patient ownership and long-term decision-making.
• Why lower-middle-market deal activity has slowed as financing costs have increased.
• How transparent communication and flexible deal structures can build seller trust.
• Why operations may offer a stronger value-creation opportunity than pricing or M&A.
• The importance of retaining, developing and incentivising key employees.

Timestamps

00:00 Paul’s background and the launch of Isaac Management
01:27 A permanent-capital approach without a traditional PE fund
02:24 The biggest acquisition mistake: overleveraging
04:50 Deal trends across the lower middle market
06:46 The valuation gap between buyers and sellers
08:39 Tariffs, financing costs and portfolio-company pressure
11:05 Chief Outsiders
12:32 Building an investment firm without institutional backing
15:28 From the search-fund concept to permanent capital
16:56 Why long-term ownership resonates with business founders
19:48 Lessons from seller conversations and dealmaking
21:18 Equity rollovers, seller financing and deal preparation
23:08 The most effective lower-middle-market growth lever
25:03 Talent retention and the true cost of replacing employees
26:31 Employee ownership and long-term engagement
27:00 Paul’s recommended media and publications
27:58 How to contact Paul Isaac

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

In this episode of The Private Equity Podcast, Alex Rawlings speaks with Russ Roenick, Co-Founder and Managing Partner at Transom Capital, about building a differentiated middle-market investment strategy around carve-outs, special situations and operational complexity.

Russ explains how launching Transom shortly before the global financial crisis shaped the firm’s highly hands-on approach. He outlines how Transom identifies businesses with strong underlying industry potential but significant operational challenges, then applies a disciplined value-creation model to improve performance.

The discussion covers Transom’s six core operational transformations: salesforce effectiveness, new product innovation, digital transformation, supply-chain improvement, cost reduction, and talent and culture.

Russ also shares how the firm structures its operations team, why former portfolio-company CEOs and CFOs can become highly effective operating partners, and how Transom is deploying AI across back-office and commercial functions.

Key Takeaways

• Why operational and situational complexity can create attractive entry points.
• How Transom approaches carve-outs as an opportunity rather than simply additional risk.
• The importance of building repeatable operational capabilities instead of attempting every possible transformation.
• Why operating teams should be involved from underwriting through execution.
• How supply-chain improvements have generated substantial gross-margin expansion.
• Where AI is currently delivering value across accounts payable, receivables, customer service, forecasting and sales.
• Why portfolio companies need internal AI champions to drive adoption.
• How leaders can stay informed without overpowering portfolio-company management teams.

Timestamps

00:00 Introduction to Russ Roenick and Transom Capital
00:30 Moving from McKinsey into Private Equity
01:26 Transom’s value-oriented investment strategy
01:55 Distressed investing versus operational value investing
03:16 Using operational and situational complexity
04:14 Carve-outs, lender situations and tail-end funds
05:14 Launching Transom during the global financial crisis
07:04 The importance of adapting while maintaining investment discipline
08:29 Why Transom specialised in carve-outs and special situations
10:58 Why many firms view carve-outs as excessive risk
12:54 Transom’s six operational transformation strategies
13:23 Salesforce transformation
14:17 New product innovation
14:45 Digital transformation and AI implementation
15:15 Supply-chain and gross-margin improvement
16:13 Cost reduction, talent and culture
17:37 Structuring the portfolio operations team
18:05 Recruiting former portfolio-company CEOs and CFOs
19:59 Transom’s approach to AI adoption
20:57 Applying AI across back-office functions
21:49 Creating internal AI champions
22:48 Common AI use cases across the portfolio
24:10 How Russ stays informed
25:31 Leadership, decision-making and knowing when to step back
25:57 How to contact Russ

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

In this episode of The Private Equity Podcast, Alex Rawlings speaks with Daniel Pianko, Co-Founder of Achieve Partners, about Achieve’s talent-led investment strategy, its $465 million exit of Optimum, and how the firm reached top 5% performance for DPI in Cambridge Associates’ US buyout benchmark.

Daniel shares how Achieve Partners invests in businesses where the biggest growth constraint is access to trained talent. Rather than simply competing for experienced hires, Achieve builds apprenticeship-style programmes inside portfolio companies, creating new talent pipelines that drive revenue, margin expansion, retention, and differentiated value creation.

The conversation explores the relationship between private equity firms and operators, why data-driven decision-making matters, how Achieve partners with universities and underrepresented talent pools, and why doing good and generating alpha do not need to be in conflict.

Key Takeaways:

• Private equity firms should empower operators to challenge assumptions with data.
• Achieve invests where talent shortages can be solved through focused training.
• Apprenticeships can increase capacity, margins, retention and scalability.
• Optimum shows how training pathways can unlock healthcare IT growth.
• Strong impact and strong returns can reinforce each other.

Timestamps:

00:03 – Introduction to Daniel Pianko and Achieve Partners
00:29 – Daniel’s career path and linking social impact with financial return
01:52 – The mistake PE firms and portfolio companies make in the boardroom
03:44 – How to avoid PE investors driving strategy without enough data
05:10 – Achieve’s unique strategy: investing where talent shortages constrain growth
06:38 – Building apprenticeship programmes to solve supply-demand talent gaps
07:08 – Daniel’s Goldman Sachs training experience and how it shaped Achieve’s model
08:25 – Rebuilding the talent pyramid in lower middle market companies
09:49 – Why Achieve focuses on business services, tech services, and healthcare services
11:12 – Building talent programmes at the portfolio company level
12:10 – Solving the gap between university education and first jobs
13:04 – Why companies should stop searching for “purple squirrels”
14:58 – Partnering with universities and building access to talent
16:44 – The Optimum exit: $465 million sale to Infosys
17:12 – Optimum’s healthcare IT thesis and value creation plan
19:00 – Building healthcare IT training pathways with universities and industry bodies
20:56 – Challenges in expanding Optimum beyond its historic core
22:24 – How Achieve reached top 5% DPI performance
22:50 – Why Achieve sells when the underwriting target is achieved
23:42 – How training programmes create a natural exit point
25:07 – Aligning impact with alpha creation
27:31 – Talent arbitrage, underrepresented communities, and overlooked graduates
29:40 – Why solving major social problems can create superior returns
30:08 – Daniel’s recommended podcasts, books, and shows
31:57 – How to contact Daniel Pianko
32:23 – Closing remarks

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

In this episode of The Private Equity Podcast, Alex Rawlings speaks with David Bell, former Wharton Professor of Marketing and early-stage investor in consumer companies including Diapers.com, Warby Parker, Harry’s and Jet.com. David shares what he looks for in standout consumer brands, why founder insight and capital discipline matter, and how businesses can build emotional and symbolic value around everyday products.

David explains why great consumer companies often begin with a simple frustration: what is wrong with the status quo? From buying diapers online to rethinking eyewear pricing, the best founders identify a clear customer problem, build a strong proposition, and execute with precision. He also discusses why overcapitalisation can damage consumer brands, using Allbirds and Casper as examples of businesses that grew quickly but struggled to sustain value.

The conversation explores omnichannel distribution, brand storytelling, cultural relevance and genuine product innovation. David highlights Touchland, Warby Parker, Native, EOS, Hello and Happy, showing how founders can elevate mundane categories through design, positioning and customer experience.

Key Takeaways:

•  Great consumer investments often start with a visceral customer problem. 
•  Capital efficiency is critical because consumer exits rarely match software-scale outcomes. 
•  Strong brands combine functional, emotional and symbolic value. 
•  D2C alone is rarely enough; winning brands need a measured omnichannel strategy. 
•  The next wave of consumer winners needs real product innovation, not just better go-to-market. 
•  Founder obsession with small details in design, scent, usability and narrative creates differentiation. 

Timestamps:
 00:03 – Introduction to David Bell and his journey from New Zealand to New York
 01:00 – David’s background at Wharton and investing in consumer companies
 01:28 – What attracted David to early winners like Diapers.com
 02:19 – Why Diapers.com solved a fundamental customer pain point
 03:15 – The importance of insight, execution and market size
 03:44 – Lessons from Allbirds and the dangers of overcapitalisation
 05:32 – How great consumer brands scale beyond the early stage
 06:27 – The shift from pure D2C to omnichannel distribution
 07:52 – Why strategic buyers value brands with retail traction
 09:18 – Why some consumer brands fail to sustain momentum
 10:11 – Touchland and the reinvention of hand sanitiser
 11:33 – Cultural relevance, collaborations and emotional connection
 12:03 – Sponsor message from Grata
 12:32 – What makes a brand fundamentally strong
 13:29 – Diapers.com and the power of descriptive branding
 14:26 – Warby Parker’s storytelling, fairness and American heritage
 15:49 – Building cognitive associations through brand activations
 17:40 – How much brand success is intentional versus luck
 18:09 – Opportunities in legacy consumer categories
 19:24 – Why obsessive attention to detail matters
 20:19 – Craig Dubitsky, EOS, Hello and elevating mundane products
 21:15 – Happy Coffee and design-led differentiation
 22:14 – Where the consumer industry is today
 22:43 – Capital-efficient growth and the Native deodorant example
 23:39 – Why real product innovation now matters more than ever
 24:36 – What David reads, watches and listens to
 25:04 – Identifying white spaces in health, wellness and longevity
 26:30 – Consumer opportunities through cultural arbitrage
 27:27 – Lessons from Coca-Cola’s global distribution and brand power
 28:24 – How to connect with David Bell
 28:52 – Closing remarks

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

In this episode, Alex Rawlings speaks with Adil Taha, a private equity operator specialising in the UK legal sector. They explore why private equity has struggled to scale law firms, the challenges of buy-and-build strategies, and why many legal businesses are weaker than they appear financially.

Adil shares lessons from rescuing and rebuilding Child & Child, explains why consumer legal services are attracting the most PE interest, and discusses how law firms differ from other professional services businesses. The conversation also covers the impact of AI, rising salary costs, partnership structures, and why the US legal market may offer bigger opportunities for investors.

Topics Covered

•  PE investment trends in legal services 
•  The Child & Child turnaround 
•  Why law firms are difficult to scale 
•  Problems with traditional partnership models 
•  Why buy-and-build strategies are struggling 
•  Consumer legal services vs full-service firms 
•  The role of AI and rising costs in legal 
•  Why the US market is attracting PE attention 

Timestamp Highlights

• 00:00 – Introduction to Adil Taha 
• 02:29 – Child & Child acquisition and turnaround 
• 09:11 – Where PE is investing in legal 
• 14:55 – The hidden weaknesses in law firms 
• 26:51 – Why professional services are hard to scale 
• 35:23 – Investment strategies that may work in legal 
• 45:05 – Why PE is looking toward the US market 

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

In this episode, Alex Rawlings speaks with Shiv Narayanan, CEO of How to SaaS, about how private equity firms can use marketing and AI as value creation levers. They discuss why many B2B companies underinvest in marketing, how AI is changing buyer behavior, and why brand authority and content are becoming critical for growth.

Timestamps

• 00:03 – Introduction to Shiv Narayanan and How to SaaS
• 01:55 – Common marketing mistakes in PE-backed businesses
• 04:15 – Finding the right marketing strategy and spend
• 08:06 – How PE firms should assess CMOs
• 12:49 – AI as a value creation lever
• 14:40 – How AI search is changing buyer behavior
• 16:02 – Why brand authority matters more than ever
• 17:54 – AI agents and the future of marketing teams
• 20:20 – The importance of investing in content
• 22:44 – Why podcasts and video are growing in B2B marketing
• 24:22 – The risk of overusing AI-generated content
• 25:21 – Shiv’s books and final advice

Key Takeaways

• Many B2B companies rely too heavily on sales and underinvest in marketing.
• Strong CMOs focus on revenue, forecasting, and enterprise value creation.
• AI platforms like ChatGPT are reshaping how buyers research solutions.
• Businesses need strong brands and quality content to remain visible.
• Podcasts, YouTube, and thought leadership content are becoming essential.

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

In this episode of the Raw Selection Private Equity Podcast, Alex Rawlings speaks with Christina Haxton about the relationship between private equity firms and portfolio company leadership teams.

They discuss how trust, communication, alignment, and culture impact execution during periods of rapid growth — and why many businesses struggle not because of strategy, but because of leadership friction and organizational disconnect.

Timestamps

00:00 – Introduction to Christina Haxton
01:27 – Common execution and leadership friction points
03:14 – Managing PE expectations vs operational reality
05:10 – Early warning signs of leadership misalignment
07:32 – Why strategy must be co-created
09:27 – Building trust between CEOs and PE firms
11:44 – What makes a compelling company vision
17:34 – Scaling quickly without burning out teams
21:12 – Why speed without alignment creates fragility
23:02 – The importance of constructive conflict
24:53 – Leadership resources and practical tools
29:32 – How to connect with Christina

Key Takeaways
Execution issues often come from unclear accountability and avoided conversations.
PE firms and executive teams need alignment on goals, timelines, and expectations.
Strong culture and trust are essential for sustainable growth.
Vision must emotionally engage teams — not just focus on financial targets.
Speed without alignment creates stress, confusion, and burnout.
Resources Mentioned
Scaling Up by Verne Harnish
The Five Dysfunctions of a Team by Patrick Lencioni
BE 2.0 by Jim Collins

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