Venture with Grace Podcast
Guest: Rachel Holt, General Partner at Construct Capital
Host: Grace Gong
Date: November 19, 2025
Episode Theme: Modernizing Supply Chain & Mobility, Building Venture Funds with Operational DNA

EPISODE OVERVIEW

This episode features Rachel Holt, co-founder and General Partner at Construct Capital, discussing her career journey from Bain and Uber to founding one of the most impactful venture funds investing in foundational industries (e.g., supply chain, logistics, manufacturing, mobility). The conversation delves deep into lessons learned scaling Uber, the nuances of general management and operational excellence, strategies behind Construct Capital's concentrated portfolio, and Rachel's partnership dynamic with Dana Grayson.

KEY DISCUSSION POINTS & INSIGHTS

Rachel Holt’s Early Career Lessons (00:08–06:30)

• Academic to Business: Rachel describes coming from a family of academics and pivoting to business—first at Bain, then interning at MLB Advanced Media, which became formative for understanding operational roles in digital companies.
• Broadening Skills: At Clorox and Stanford, she gained general management and marketing fundamentals. She emphasizes targeting company roles connected to core revenue-driving functions:
  • “You want to do what a company does to make money. Those are the functions that are really going to be the power centers and the decision makers.” (05:00)

Lessons from Early Uber & the Power of General Management (06:30–13:20)

• Joining Uber (2011): Rachel was one of the early hires, running Uber DC as a “CEO of your city” in a super decentralized, collaborative environment:
  • “It was kind of this risk-free way to be an entrepreneur… as soon as you figured something out… you would share it with the NY GM, SF GM. Super collaborative.” (05:50)
• Generalist Skills: Rachel explains that being a strong generalist and a problem solver was more important than having deep expertise in one area.
  • “I was pretty good at everything but didn’t necessarily spike on any one thing… That’s part of being a GM.” (07:26)
• No Playbook: She recalls being forced to solve problems (like handling surprise regulatory fights) without precedent or formal training, learning “on the fly”:
  • “There wasn’t a playbook… it was about problem solving.” (07:55)

Navigating Ambiguity, Collaboration vs. Competition (13:20–18:36)

• Collaboration Culture:
  • The decentralized Ops teams ran mini-AB tests in each city and then quickly shared best practices. This mentality rooted in shared incentives—everyone thrived if the company grew, not from internal competition.
  • “If the company is growing quickly, your trajectory is growing at the rate the company is growing. The best thing you can do is join a great startup and hang on.” (14:25)
• Decentralization's Power: Rachel discusses how fast-growing startups should prioritize speed, which fits decentralized team models. Accountabilities, visibility, and transparency are critical.
  • “There was deep sense of metric visibility… [and] accountability. You were responsible for knowing your metrics and could explain to the whole company.” (18:36)

Org Design Trade-offs—When (De)centralization Matters (22:23–24:26)

• Optimize for Strategy: Decentralization works when optimizing for speed and innovation. For consistency/compliance, centralization is better.
  • “If compliance is the core, that speaks to more centralization… There are trade-offs that come with every structure.” (22:50)

Transition to Construct Capital – From Operator to Fund Manager (24:26–32:32)

• Construct’s Focus:
  • Investing in foundational industries—supply chain, mobility, logistics—because these sectors are “deeply underinvested in tech” with “massive TAM and little incumbent competition.”
  • “We were probably a hair early—which is where you want to be in venture—around this thesis.” (28:00)
• Fundraising:
  • Construct went out in 2020, just pre-COVID, and still managed to oversubscribe its first fund, now activating a third.
  • “Here we were—a first time partnership, first time fund, trying to get through… all LPs hadn’t met in person!” (29:00)
• Portfolio Model:
  • Deliberately small and concentrated portfolios; deep, hands-on support for founders.

The Construct GP Partnership & Inclusive Team Model (32:32–38:46)

• Complementarity with Co-Founder Dana Grayson:
  • Rachel’s operator background plus Dana’s venture experience was key:
    • “It’s one of the most important decisions—a cofounder relationship... We were in the same phase of life and wanted to build for the next 20 years.” (33:23)
  • No deal attribution at Construct—all partners are aligned and incentivized across the portfolio.
    • “No one is more incentivized to help some companies than others… extremely team-based approach.” (34:49)
• Firm Incentives:
  • All employees (even office staff) have carry in the fund. Accountability maintained via quarterly portfolio reviews.
    • “We run Construct like a startup. If you aren’t contributing, you won’t be here for the long term.” (38:46)

Construct’s Investment Approach & Process (40:29–47:57)

• Portfolio Construction:
  • ~25 companies/fund, most investments leading or co-leading at seed, remainder at Series A.
  • Team assigns clear responsibilities for value-add quarterly, reviews execution vs. plan.
• Fundraising Approach:
  • Focused on institutional LPs for long-term commitments. Caps fund sizes for strategic discipline.
    • “Discipline is important… $3-5 million dollar checks really matter to us.” (45:00)

Institutional VC vs. Angel Investing; Diligence as Value (47:57–51:22)

• Different Expectations: Institutions expect you to lead, underwrite, and form a thesis, not just source intros.
  • “You don’t outsource the diligence process… a good investor pulls together data points around the founder, team, technology, market, and product.” (48:31)

End-to-End Support & Sector Focus (51:22–56:12)

• Lifecycle Partnership:
  • Construct aims to support founders from first check through M&A or IPO, not just to the next round.
    • “Dana’s seen companies from seed to IPO; I was at Uber from Series A to IPO… You need investors who have seen the full lifecycle.” (54:12)

NOTABLE QUOTES & MEMORABLE MOMENTS

• On General Management:
  “I was pretty good at everything, but didn’t necessarily spike on any one thing. That’s part of being a GM—it’s about problem-solving across different arenas day to day.”
  —Rachel Holt (07:26)

• On Startup Growth:
  “The best thing you can do for your career, particularly if you join a startup, is join the right startup and hang on. Your trajectory is growing as fast as the company.”
  —Rachel Holt (14:25)

• On Decentralized Teams:
  “The beauty of decentralized teams is speed… you have AB tests running in every city. But those only matter if the best things are shared.”
  —Rachel Holt (16:40)

• On Fund Building:
  “When we went into the fund’s thesis, we were probably a hair early—which is kind of where you want to be on the venture side.”
  —Rachel Holt (28:00)

• On Team Economics:
  “At a startup, everyone was incentivized to contribute because they had carry. Same here—every long-term role at Construct has carry, including our office manager. That doesn’t exist at most places.”
  —Rachel Holt (38:46)

TIMESTAMPS FOR IMPORTANT SEGMENTS

• 00:08–06:30 — Rachel’s early career journey and key foundational lessons
• 06:30–13:20 — Uber’s early days, learning by doing, and the generalist problem-solver’s edge
• 13:20–18:36 — Collaboration, sharing best practices, and the incentive structures at Uber
• 22:23–24:26 — When to decentralize vs. centralize: strategy and org design trade-offs
• 24:26–32:32 — Founding Construct Capital, raising funds, and sector thesis
• 32:32–38:46 — GP partnership, “no attribution” model, and inclusive incentives
• 40:29–47:57 — Portfolio construction, investment cadence, LP management, and fundraising strategy
• 47:57–51:22 — Angel vs. institutional VC; diligence, value-creation, and process
• 51:22–56:12 — Thesis-driven sourcing, supporting founders through full lifecycle
• 56:12–57:33 — Fire round (Rachel’s book pick, dinner guests, role models)

FIRE ROUND MINI-SECTION (56:12–57:33)

• Favorite book: American Kingpin by Nick Bilton (“for the adults, not the kids!”)
• Dinner party guest: “Serena Williams.”
• Biggest career impact: “Travis [Kalanick].”
• Where to find Rachel: “At work, with my family as much as possible, and on the tennis court.”

FINAL THOUGHTS

Rachel Holt’s operating muscle and candid storytelling deliver a masterclass on building in high-speed environments, architecting team-wide incentives, and approaching venture with intentional, thesis-driven focus. For founders, operators, or aspiring VCs, this episode offers actionable frameworks and a glimpse into how category-defining firms are built.

Listen to the full episode for deeper insight, stories, and practical advice on scaling startups and funds in infrastructure and tech.