In this episode, Alex Rawlings is joined by Henry Ward, CEO and Co-Founder of Carta, to explore the evolving landscape of private equity and venture capital through the lens of software, operations, and professionalization. Henry shares his journey building Carta into a multi-billion-dollar software business and how it’s transforming the infrastructure of private markets.

Henry dives into why private equity must evolve from its legacy of financial engineering to an operational value-add model—and how the next generation of firms is doing just that. He also unpacks Carta’s roadmap for building cloud-native tools for PE firms, including fund accounting, cap tables, waterfalls, and LP portals. Plus, he explains the two-speed mentality of balancing venture-style growth with private equity-level rigor—and what he’s learned along the way.

🕰️ Timestamps:
00:03 – Welcome and introduction to Henry Ward and Carta
00:29 – Carta’s mission and Henry’s background
00:58 – The outdated mindset in legacy PE firms
01:40 – Hard lessons building a multi-S-curve business
04:02 – Scaling in small markets and fast saturation
05:22 – Innovating inside a scaled company (recommendation: Loonshots)
07:18 – What Henry would do differently (spoiler: gather more info, faster)
09:41 – Grata ad spot
10:09 – Carta’s three-layer approach in venture: cap tables, fund ops, LP portals
12:54 – Applying the same playbook to private equity and private credit
13:50 – The speed of reporting in PE is accelerating—software must follow
14:48 – Why PE and VC have lagged in professionalization
16:15 – Influence of firms like Andreessen Horowitz in redefining fund operations
17:42 – Back-office vs strategic finance in PE firms
18:42 – Competition and differentiation are driving the need for change
19:37 – What should PE automate first? Fund accounting
20:36 – AI disruption in accounting and the end of manual debits and credits
22:03 – Cloud adoption in PE is still lagging—40% still on-prem!
22:31 – Balancing venture-style growth and PE-style discipline on Carta’s cap table
24:56 – Strategic value of PE investors when aligned with product growth
25:24 – Henry’s reading habits and framework (read the ends, skip the middle)
26:53 – Timeless business books and staying current with The Economist
27:23 – How to contact Henry

📌 Key Takeaways:

• PE is shifting from financial engineering to operational alpha.
• The professionalization of private equity firms is overdue and underway.
• Carta is bringing fund accounting, cap tables, and LP ops into the cloud.
• PE must adopt tech to compete, especially as investor and platform competition heats up.
• Automation of accounting and reporting is the low-hanging fruit for transformation.
• Balancing growth and discipline requires the right capital partners—and Carta has both.

📨 Connect with Henry Ward:
📧 Email: henry@carta.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

David Feingold, CEO of Broad Street Global, joins us on The Private Equity Podcast to share his 35+ year journey from law to leading one of the largest infrastructure-focused PE firms in the U.S. He unpacks lessons in leadership, hiring, culture, and why they’ve entered crypto mining. This episode is a masterclass in building high-performing teams and seizing unconventional opportunities.

[00:00] Welcome and intro to David Feingold and Broad Street Global – infrastructure + crypto investing

[00:29] David’s background – lawyer-turned-PE exec with 35+ years of experience

[00:57] Early academic honors and mentorship from T. Boone Pickens

[01:25] The power of people over business models – hiring philosophy

[01:53] Letting people do what they’re good at drives performance

[02:19] 55 partners, zero attrition – proof that culture and fit matter

[02:48] No politics, shared vacations – how Broad Street fosters cohesion

[03:15] Lessons from early hiring mistakes – focus on listening

[03:43] Listening is undervalued – why it’s his #1 executive skill

[04:40] Decentralized control – empowering division heads like CEOs

[05:11] Weekly Zooms, collaborative decision-making with 20 reports

[05:39] Entrepreneurship mindset among leadership breeds buy-in

[06:04] Decision rights create ownership and reduce bottlenecks

[06:58] Turnover test post-bonus – why Broad Street retains top talent

[07:26] High comp + real input = long-term loyalty

[08:16] Happiness at work impacts life – no "Yoda talk," just results

[08:46] All 55 partners signed up for Navy SEAL training – by choice

[09:44] Traditional infra + crypto mining – what’s the link?

[10:12] Real estate + utility relationships gave them a crypto edge

[11:09] Enter Dogecoin early – before Elon Musk moved the market

[11:37] Built North America’s largest Dogecoin mining operation

[12:06] Opportunistic scaling based on margin and fit

[12:53] Infra skills + land + utility access = expansion blueprint

[13:22] Mars joke, but serious point: go where profit meets capability

[13:49] Trends in U.S. infrastructure – high barriers, high demand

[14:14] Housing shortage drives demand – focus on Carolinas

[14:43] Greenville top retirement spot – strong absorption rates

[15:10] Long runway – next 2–3 generations will stay in this sector

[15:39] What he reads/listens to: all business podcasts + global news

[16:09] Constant learning – 45 mins daily to stay sharp

[16:37] Ideas from people > articles – value of conversations

[17:07] Investors wanted a brokerage – he built one

[17:37] Always talking to the market – shaping services around demand

[18:05] Education goal: answer any question, any time

[18:33] Avoid "I don’t know" as CEO – credibility matters

[19:02] Always studying: legal, financial, geopolitical trends

[19:59] Website contact – happy to connect

[20:27] Outro – thank you and wrap-up

How to connect with David Feingold? via BroadStreetPrivateEquity or LinkedIn

Subscribe for more episodes on iTunes & Spotify

Got feedback or questions? Email Alex at alex.rawlings@raw-selection.com. Until next time—keep smashing it!

Raw Selection part

Fundraising in 2025 isn’t business as usual. James Varela, Partner at Rede Partners and Head of MENA, joins us to break down what it really takes to raise capital from LPs—especially in the Middle East. We talk DPI pressure, LP targeting, co-investments, how to build credibility in emerging markets, and the biggest mistake GPs still make when pitching. Whether you’re struggling or oversubscribed, this one’s for you.

[00:00] Intro to James Varela and focus on capital raising in the Middle East.

[00:30] James’ 15+ years in capital raising across PE, infra, credit, and real estate.

[01:26] Fundraising remains tough—macroeconomics and low DPI are key issues.

[02:21] LPs cautious; focus shifting to GP quality and DPI visibility.

[03:13] GPs turning to NAV lending and creative liquidity tools.

[04:05] 66% of LPs now cite DPI as their top investment metric.

[04:31] Strong fundraises begin 12 months out—prep is everything.

[05:00] Nail your equity story—what sets you apart?

[05:26] Focus on LPs where your strategy fits—don’t spray and pray.

[05:55] Transparency and respect matter more than past returns.

[06:26] GPs often fail to systematize and name their edge.

[07:25] LPs want proof—not theory—of execution and outcomes.

[08:24] Plan 2–3 years out for Middle East fundraising; co-invests are key.

[08:55] Content > presence—show up with something to say.

[09:52] LPs want honest differentiation, not polished fluff.

[10:51] Share what went wrong and what changed—credibility counts.

[11:44] Most firms struggle from poor positioning, not poor product.

[12:14] Systems reduce risk, especially for global firms.

[13:37] Frameworks matter—manage what’s out of your control.

[14:07] Even top performers can fail at storytelling.

[15:02] Reframing the narrative can unlock overlooked value.

[16:26] Fundraising is marketing—Rory Sutherland’s Alchemy cited.

[17:22] Iteration is painful but critical—change takes work.

[18:20] LPs care about the future, not just past returns.

[19:09] Big firms re-entering mid and small-cap to chase alpha.

[19:37] Middle East mistakes: wrong timing, same pitch, poor targeting.

[20:34] Use portfolio milestones as conversation openers.

[21:04] GCC LPs want both long-term trust and large co-invests.

[21:59] Vision and culture alignment matter just as much.

[22:29] Targeting is everything—don’t chase irrelevant LPs.

[22:59] LPs prefer North America, large GPs, proven track records.

[23:57] Specialization and sector depth are rising priorities.

[24:55] AI and tech are hot in the UAE—substance still matters.

[25:54] Growing appetite for GP stakes from Middle East LPs.

[26:21] Europe gaining ground as LPs move down-market.

[27:14] Top reads: Alchemy, Acquired, Diary of a CEO, Tools of Titans, Atomic Habits.

[29:05] Final thoughts: fundraising is either brutal—or it’s fine. Nothing in between.

Connect with James Varela on LinkedIn. Thanks for tuning in.

Subscribe for more episodes on iTunes & Spotify

Got feedback or questions? Email Alex at alex.rawlings@raw-selection.com. Until next time—keep smashing it!

Raw Selection partners with Private Equity firms and their portfolio com