Why fundraising never gets easier

What does it really take to raise a venture fund—and why does fundraising never get easier, even at Fund 5 or Fund 6? In this episode, I talk with Yasmine Lacaillade, Founder of Sinefine and one of the most respected capital formation leaders in venture. Yasmine shares her journey from TPG Axon in London to joining Drive Capital at Fund I—years before it became consensus. We discuss why fundraising is always difficult, how LP sentiment shifts every 2–3 years, and why top fundraisers treat the process like enterprise sales rather than relationship maintenance. Yasmine breaks down her market mapping framework, why the top of the funnel must always stay wide, how to qualify LPs quickly, and why “adding value first” is her core operating principle. She also explains how she evaluates new managers, how to identify true LP demand today, and why people, culture, and team cohesion matter more than anything else in venture.

Highlights:

• How moving from London to Columbus led Yasmine into the earliest days of Drive Capital.
• Why she joined Drive at Fund I—and what she saw before LPs did.
• Why fundraising never gets easier, even after multiple successful vintages.
• How LP priorities, liquidity, and macro cycles shift every 2–3 years.
• The difference between networking vs. honing existing relationships.
• Why Yasmine treats fundraising like enterprise sales—and why a huge top of funnel is essential.
• What LPs are actually looking for in a first meeting
• How to qualify LPs quickly by asking exactly what they’ve invested in over the last 6–12 months.
• Why the most important skill in fundraising is mapping the market and respecting LPs’ time.
• How Sinefine structures a new engagement with a GP—from deck narrative to LP segmentation.
• Why she only works with a handful of managers and how she selects them.
• How she evaluates team cohesion and founder intensity
• Why her philosophy is to add value before asking for anything.
• The psychology of transactional vs. non-transactional relationships and the idea of “goodwill reservoirs.”
• Why she shut down her fund-of-funds product and how she built Sinefine into a product-oriented platform.
• How Zoom culture has changed LP behavior, time allocation, and transparency.
• The importance of story evolution, narrative sharpening, and portfolio math in venture.

Guest Bio:

Yasmine Lacaillade is the Founder of Sinefine, a capital formation and institutional fundraising advisory firm working with top-tier venture managers. Before launching Sinefine, Yasmine spent over a decade in investment and fundraising roles, including at TPG Axon in London and as an early team member at Drive Capital, where she helped build one of the leading venture franchises in the Midwest from its first fund onward. Yasmine specializes in market mapping, LP strategy, investor relations, and helping emerging and established GPs navigate complex fundraising environments. She is widely recognized for her clarity of thinking, LP intelligence, and ability to guide managers through the entire capital formation journey.

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X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Yasmine Lacaillade: https://www.linkedin.com/in/yasmine-lacaillade-6448888/

Links Sinefine: https://www.sinefine.co/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Introduction (3:08) Fundraising challenges in venture capital vs. hedge funds (5:00) Networking and managing relationships in fundraising (9:12) Balancing relationships with the transactional nature of fundraising (13:22) Market mapping and targeting LPs effectively (17:02) Long-term investment decisions and adapting to market conditions (21:58) Building trust in first meetings with LPs (27:36) Transactional relationships and adding value in LP-GP dynamics (31:08) Onboarding a new fund and quick trust-building (34:44) Pursuing relationships with potential managers and the Ashton Kutcher investing principle (38:45) Balancing personal and professional commitments (40:06) Embracing people-pleasing as a strength in investing (42:49) Reputation and value creation in the investment world (44:31) Passion for venture capital and finding excitement in buyouts (49:30) Team cohesion and investment success (50:09) Closing