StarZero All shows Try the podcast clipper →

Jul 20, 2015 · 24m · 20vc

20 VC 055: VC Done Right with Jonathon Triest @ Ludlow Ventures

Jonathan Triest · 16m spoken Harry Stebbings · 5m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this episode of The 20 Minute VC, host Harry Stebbings interviews Jonathan Triest, founder and managing director of Ludlow Ventures, discussing his unconventional background, Ludlow's founder-first investment philosophy, creative deal sourcing mechanisms, and the critical role of mentorship.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 25.1% of the talking time here. How this is scored →

Harry as informed peer 2.4 Guest teaching 2.4 Guest disagreement 1.8 Harry pushing back 2.0
05100:0010:0020:001:36–4:30 · Harry as informed peer 2/10 Jonathan Triest's Unconventional Path into Venture Capital The host asks light introductory questions about Jonathan's unconventional entry into VC. Jonathan shares his design background and early mistakes playfully, while the host jokes along and probes briefly for a specific mistake.4:32–9:04 · Harry as informed peer 2/10 Ludlow Ventures' Philosophy and Fund Growth Jonathan explains Ludlow's founder-centric philosophy and fund trajectory. The host probes on whether early fund success came from one single deal and asks about LP dynamics.9:05–13:20 · Harry as informed peer 3/10 Deal Sourcing, Differentiation, and Creative Vehicles Jonathan reframes the host's premise about competing with mega-funds like Andreessen Horowitz, explaining that seed funds act as a funnel rather than competitors. He then details unique deal-sourcing initiatives like the Sandwich Fund.13:28–19:42 · Harry as informed peer 3/10 Evaluating Founders, Design Values, and High-Caliber Mentors The host brings industry quotes from Jason Calacanis and references upcoming guests like Brad Feld to guide the interview. Jonathan shares how he recruited top-tier mentors despite having little leverage.19:44–23:28 · Harry as informed peer 2/10 Quickfire Round and Recent Investments Jonathan playfully subverts standard quickfire expectations with non-traditional answers and flips a question back onto the host before revealing his latest investment.1:36–4:30 · Guest teaching 1/10 Jonathan Triest's Unconventional Path into Venture Capital The host asks light introductory questions about Jonathan's unconventional entry into VC. Jonathan shares his design background and early mistakes playfully, while the host jokes along and probes briefly for a specific mistake.4:32–9:04 · Guest teaching 2/10 Ludlow Ventures' Philosophy and Fund Growth Jonathan explains Ludlow's founder-centric philosophy and fund trajectory. The host probes on whether early fund success came from one single deal and asks about LP dynamics.9:05–13:20 · Guest teaching 4/10 Deal Sourcing, Differentiation, and Creative Vehicles Jonathan reframes the host's premise about competing with mega-funds like Andreessen Horowitz, explaining that seed funds act as a funnel rather than competitors. He then details unique deal-sourcing initiatives like the Sandwich Fund.13:28–19:42 · Guest teaching 2/10 Evaluating Founders, Design Values, and High-Caliber Mentors The host brings industry quotes from Jason Calacanis and references upcoming guests like Brad Feld to guide the interview. Jonathan shares how he recruited top-tier mentors despite having little leverage.19:44–23:28 · Guest teaching 3/10 Quickfire Round and Recent Investments Jonathan playfully subverts standard quickfire expectations with non-traditional answers and flips a question back onto the host before revealing his latest investment.1:36–4:30 · Guest disagreement 1/10 Jonathan Triest's Unconventional Path into Venture Capital The host asks light introductory questions about Jonathan's unconventional entry into VC. Jonathan shares his design background and early mistakes playfully, while the host jokes along and probes briefly for a specific mistake.4:32–9:04 · Guest disagreement 1/10 Ludlow Ventures' Philosophy and Fund Growth Jonathan explains Ludlow's founder-centric philosophy and fund trajectory. The host probes on whether early fund success came from one single deal and asks about LP dynamics.9:05–13:20 · Guest disagreement 3/10 Deal Sourcing, Differentiation, and Creative Vehicles Jonathan reframes the host's premise about competing with mega-funds like Andreessen Horowitz, explaining that seed funds act as a funnel rather than competitors. He then details unique deal-sourcing initiatives like the Sandwich Fund.13:28–19:42 · Guest disagreement 1/10 Evaluating Founders, Design Values, and High-Caliber Mentors The host brings industry quotes from Jason Calacanis and references upcoming guests like Brad Feld to guide the interview. Jonathan shares how he recruited top-tier mentors despite having little leverage.19:44–23:28 · Guest disagreement 3/10 Quickfire Round and Recent Investments Jonathan playfully subverts standard quickfire expectations with non-traditional answers and flips a question back onto the host before revealing his latest investment.1:36–4:30 · Harry pushing back 2/10 Jonathan Triest's Unconventional Path into Venture Capital The host asks light introductory questions about Jonathan's unconventional entry into VC. Jonathan shares his design background and early mistakes playfully, while the host jokes along and probes briefly for a specific mistake.4:32–9:04 · Harry pushing back 2/10 Ludlow Ventures' Philosophy and Fund Growth Jonathan explains Ludlow's founder-centric philosophy and fund trajectory. The host probes on whether early fund success came from one single deal and asks about LP dynamics.9:05–13:20 · Harry pushing back 2/10 Deal Sourcing, Differentiation, and Creative Vehicles Jonathan reframes the host's premise about competing with mega-funds like Andreessen Horowitz, explaining that seed funds act as a funnel rather than competitors. He then details unique deal-sourcing initiatives like the Sandwich Fund.13:28–19:42 · Harry pushing back 2/10 Evaluating Founders, Design Values, and High-Caliber Mentors The host brings industry quotes from Jason Calacanis and references upcoming guests like Brad Feld to guide the interview. Jonathan shares how he recruited top-tier mentors despite having little leverage.19:44–23:28 · Harry pushing back 2/10 Quickfire Round and Recent Investments Jonathan playfully subverts standard quickfire expectations with non-traditional answers and flips a question back onto the host before revealing his latest investment.

speaking balance: gold is Harry, purple is the guest (3 minute bins)

0:00 · Harry 59.4% · guest 40.6%0:00 · Harry 59.4% · guest 40.6%3:00 · Harry 12.2% · guest 87.8%3:00 · Harry 12.2% · guest 87.8%6:00 · Harry 20.4% · guest 79.6%6:00 · Harry 20.4% · guest 79.6%9:00 · Harry 5.5% · guest 94.5%9:00 · Harry 5.5% · guest 94.5%12:00 · Harry 19.1% · guest 80.9%12:00 · Harry 19.1% · guest 80.9%15:00 · Harry 15.5% · guest 84.5%15:00 · Harry 15.5% · guest 84.5%18:00 · Harry 20.2% · guest 79.8%18:00 · Harry 20.2% · guest 79.8%21:00 · Harry 32.5% · guest 67.5%21:00 · Harry 32.5% · guest 67.5%24:00 · Harry 100% · guest 0%24:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 9:05 Rejecting competitive premise

Jonathan directly rejects the host's question premise about competing with Andreessen and Sequoia, clarifying that they collaborate rather than compete.

 Hardest push from Harry ▶ 6:39 Probing fund performance sources

Harry pushes past general fund talk to ask specifically if their early profits were driven by a single outlier win or broader portfolio success.

 Biggest teaching moment ▶ 9:05 Explaining the seed-to-series-A funnel

Jonathan educates the host on venture mechanics, demonstrating how upstream series A funds rely on seed funds for deal flow rather than competing directly.

 Harry holds his own ▶ 14:23 Citing Calacanis on founder evaluation

Harry demonstrates industry knowledge by bringing up Jason Calacanis's 'eye of the tiger' concept to anchor his question on founder selection.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Jonathan Triest's Unconventional Path into Venture Capital 2112 The host asks light introductory questions about Jonathan's unconventional entry into VC. Jonathan shares his design background and early mistakes playfully, while the host jokes along and probes briefly for a specific mistake.
Ludlow Ventures' Philosophy and Fund Growth 2212 Jonathan explains Ludlow's founder-centric philosophy and fund trajectory. The host probes on whether early fund success came from one single deal and asks about LP dynamics.
Deal Sourcing, Differentiation, and Creative Vehicles 3432 Jonathan reframes the host's premise about competing with mega-funds like Andreessen Horowitz, explaining that seed funds act as a funnel rather than competitors. He then details unique deal-sourcing initiatives like the Sandwich Fund.
Evaluating Founders, Design Values, and High-Caliber Mentors 3212 The host brings industry quotes from Jason Calacanis and references upcoming guests like Brad Feld to guide the interview. Jonathan shares how he recruited top-tier mentors despite having little leverage.
Quickfire Round and Recent Investments 2332 Jonathan playfully subverts standard quickfire expectations with non-traditional answers and flips a question back onto the host before revealing his latest investment.

Statements from this episode (7)

Disclosure
Triest: Ludlow Ventures deployed $1M in its 2009 initial vehicle
“We put about a million dollars to use in 2009.”
Jonathan Triest Jul 20, 2015 ▶ 6:14
Disclosure
Triest: Ludlow Ventures raised a $16M fund in 2013
“And then we raised the proper fund in 2013. That was close to sixteen million dollars.”
Jonathan Triest Jul 20, 2015 ▶ 7:03
Insight
Triest: Corporate VCs have smaller networks because they do not fundraise
“There are certain firms who invest off balance sheets of big corporations, which is great, and they do really wonderful things, but their networks are always generally smaller and I think a lot of that has to do with the lack of fundraising, because they're no…”
Jonathan Triest Jul 20, 2015 ▶ 7:59
Disclosure
Triest: Ludlow Ventures focuses on family office LPs over institutional investors
“Yeah, I think our sweet spot is really still with high net worth individuals and family offices. Again, you know, our relationship with our LPs is very similar to our relationship with the founders we invest in. Like we're, we want to build really strong, mean…”
Jonathan Triest Jul 20, 2015 ▶ 8:25
Disclosure
Ludlow Ventures pays for startup promo videos in exchange for equity
“So the deal we struck is that we pay for the company's video, so they don't have to go out of pocket, and in exchange, Adam and Ludlow take equity in the company.”
Jonathan Triest Jul 20, 2015 ▶ 11:56
Disclosure
Triest: Once a startup enters Y Combinator, we missed our premier opportunity
“In terms of investing, once a company's in an accelerator, it depends on which accelerator, but if you take like a YC, for example, it's generally too, you know, we've kind of missed our premier opportunity to invest in the company. Our goal is to find the com…”
Jonathan Triest Jul 20, 2015 ▶ 12:53
Opinion
Triest: Outdoor advertising is stale and gross
“You know, it's a play on a, to disrupt outdoor advertising, which is just so stale and gross.”
Jonathan Triest Jul 20, 2015 ▶ 23:00
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 1,200 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.

Try the podcast clipper Learn more