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Jun 27, 2016 · 19m · top-founders

EP 338: He's 28 Investing From $600 Million Fund, $4.2 Billion Under Management

Nathan Latka · 8m spoken Michael Gilroy · 8m 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 Top, host Nathan Latka interviews Canaan Partners investor Michael Gilroy about his transition from Silicon Valley investment banking to early-stage venture capital. Gilroy details the venture funding ladder, strategic deal sourcing, vertical specialization, and career advancement within tech investing.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 51.2% of the talking time here. How this is scored →

Nathan as informed peer 4.6 Guest teaching 2.2 Guest disagreement 0.8 Nathan pushing back 2.0
05100:0010:002:00–5:05 · Nathan as informed peer 7/10 Silicon Valley Banking and the Vitrue Acquisition Nathan showcases strong domain knowledge about the 2012 tech M&A landscape, recalling Oracle's previous acquisition of Involver and Salesforce purchasing Buddy Media. Michael confirms these details and provides background on his early career. The dynamic is respectful and collaborative.5:05–8:25 · Nathan as informed peer 5/10 Transitioning from Investment Banking to Venture Capital Nathan asks Michael to elaborate on the strategic reasoning for moving from banking to VC, and Michael educates the audience on fundraising round stages from Angel to Series A and beyond. Nathan synthesizes the response accurately.8:25–11:20 · Nathan as informed peer 5/10 Sourcing Bellhops and Navigating Career Ranks in Venture Capital Nathan brings up previous guest Cam Doody from Bellhops and questions Michael on why Canaan missed the Series A round and how titles and promotions work within venture capital firms.11:20–13:34 · Nathan as informed peer 6/10 Vertical Specialization and Strategic Deal Sourcing Nathan checks Michael's portfolio companies like Tubular and Arbor against his stated focus in FinTech, teasing him about when his first FinTech deal will close.13:35–15:14 · Nathan as informed peer 0/10 Promotional Break: Austin Live Business Event and HostGator Mid-roll promotional ad break featuring host monologues for Austin Live and HostGator. No guest interaction or scoring dynamic.2:00–5:05 · Guest teaching 2/10 Silicon Valley Banking and the Vitrue Acquisition Nathan showcases strong domain knowledge about the 2012 tech M&A landscape, recalling Oracle's previous acquisition of Involver and Salesforce purchasing Buddy Media. Michael confirms these details and provides background on his early career. The dynamic is respectful and collaborative.5:05–8:25 · Guest teaching 4/10 Transitioning from Investment Banking to Venture Capital Nathan asks Michael to elaborate on the strategic reasoning for moving from banking to VC, and Michael educates the audience on fundraising round stages from Angel to Series A and beyond. Nathan synthesizes the response accurately.8:25–11:20 · Guest teaching 3/10 Sourcing Bellhops and Navigating Career Ranks in Venture Capital Nathan brings up previous guest Cam Doody from Bellhops and questions Michael on why Canaan missed the Series A round and how titles and promotions work within venture capital firms.11:20–13:34 · Guest teaching 2/10 Vertical Specialization and Strategic Deal Sourcing Nathan checks Michael's portfolio companies like Tubular and Arbor against his stated focus in FinTech, teasing him about when his first FinTech deal will close.13:35–15:14 · Guest teaching 0/10 Promotional Break: Austin Live Business Event and HostGator Mid-roll promotional ad break featuring host monologues for Austin Live and HostGator. No guest interaction or scoring dynamic.2:00–5:05 · Guest disagreement 1/10 Silicon Valley Banking and the Vitrue Acquisition Nathan showcases strong domain knowledge about the 2012 tech M&A landscape, recalling Oracle's previous acquisition of Involver and Salesforce purchasing Buddy Media. Michael confirms these details and provides background on his early career. The dynamic is respectful and collaborative.5:05–8:25 · Guest disagreement 1/10 Transitioning from Investment Banking to Venture Capital Nathan asks Michael to elaborate on the strategic reasoning for moving from banking to VC, and Michael educates the audience on fundraising round stages from Angel to Series A and beyond. Nathan synthesizes the response accurately.8:25–11:20 · Guest disagreement 1/10 Sourcing Bellhops and Navigating Career Ranks in Venture Capital Nathan brings up previous guest Cam Doody from Bellhops and questions Michael on why Canaan missed the Series A round and how titles and promotions work within venture capital firms.11:20–13:34 · Guest disagreement 1/10 Vertical Specialization and Strategic Deal Sourcing Nathan checks Michael's portfolio companies like Tubular and Arbor against his stated focus in FinTech, teasing him about when his first FinTech deal will close.13:35–15:14 · Guest disagreement 0/10 Promotional Break: Austin Live Business Event and HostGator Mid-roll promotional ad break featuring host monologues for Austin Live and HostGator. No guest interaction or scoring dynamic.2:00–5:05 · Nathan pushing back 2/10 Silicon Valley Banking and the Vitrue Acquisition Nathan showcases strong domain knowledge about the 2012 tech M&A landscape, recalling Oracle's previous acquisition of Involver and Salesforce purchasing Buddy Media. Michael confirms these details and provides background on his early career. The dynamic is respectful and collaborative.5:05–8:25 · Nathan pushing back 2/10 Transitioning from Investment Banking to Venture Capital Nathan asks Michael to elaborate on the strategic reasoning for moving from banking to VC, and Michael educates the audience on fundraising round stages from Angel to Series A and beyond. Nathan synthesizes the response accurately.8:25–11:20 · Nathan pushing back 3/10 Sourcing Bellhops and Navigating Career Ranks in Venture Capital Nathan brings up previous guest Cam Doody from Bellhops and questions Michael on why Canaan missed the Series A round and how titles and promotions work within venture capital firms.11:20–13:34 · Nathan pushing back 3/10 Vertical Specialization and Strategic Deal Sourcing Nathan checks Michael's portfolio companies like Tubular and Arbor against his stated focus in FinTech, teasing him about when his first FinTech deal will close.13:35–15:14 · Nathan pushing back 0/10 Promotional Break: Austin Live Business Event and HostGator Mid-roll promotional ad break featuring host monologues for Austin Live and HostGator. No guest interaction or scoring dynamic.

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

0:00 · Nathan 80.8% · guest 19.2%0:00 · Nathan 80.8% · guest 19.2%3:00 · Nathan 34.4% · guest 65.6%3:00 · Nathan 34.4% · guest 65.6%6:00 · Nathan 17.1% · guest 82.9%6:00 · Nathan 17.1% · guest 82.9%9:00 · Nathan 23.4% · guest 76.6%9:00 · Nathan 23.4% · guest 76.6%12:00 · Nathan 65.3% · guest 34.7%12:00 · Nathan 65.3% · guest 34.7%15:00 · Nathan 66.9% · guest 33.1%15:00 · Nathan 66.9% · guest 33.1%18:00 · Nathan 100% · guest 0%18:00 · Nathan 100% · guest 0%
Sharpest disagreement ▶ 8:49 Michael admits internal firm delays caused them to miss Series A

Michael frankly explains why Canaan was late to the Bellhops Series A deal due to internal diligence processes despite high competition.

 Hardest push from Nathan ▶ 4:37 Nathan rejects Michael's humble explanation of career success

Nathan refuses Michael's generic answer about working hard and having passion, pushing him to reveal what set him apart.

 Biggest teaching moment ▶ 6:49 Michael breaks down venture capital funding mechanics

Michael gives a structured breakdown of funding rounds from Angel and Seed through late-stage growth venture capital.

 Nathan holds their own ▶ 2:58 Nathan demonstrates 2012 tech M&A market knowledge

Nathan recalls precise details of the 2012 market including Oracle acquiring Involver and Salesforce buying Buddy Media.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Silicon Valley Banking and the Vitrue Acquisition 7212 Nathan showcases strong domain knowledge about the 2012 tech M&A landscape, recalling Oracle's previous acquisition of Involver and Salesforce purchasing Buddy Media. Michael confirms these details and provides background on his early career. The dynamic is respectful and collaborative.
Transitioning from Investment Banking to Venture Capital 5412 Nathan asks Michael to elaborate on the strategic reasoning for moving from banking to VC, and Michael educates the audience on fundraising round stages from Angel to Series A and beyond. Nathan synthesizes the response accurately.
Sourcing Bellhops and Navigating Career Ranks in Venture Capital 5313 Nathan brings up previous guest Cam Doody from Bellhops and questions Michael on why Canaan missed the Series A round and how titles and promotions work within venture capital firms.
Vertical Specialization and Strategic Deal Sourcing 6213 Nathan checks Michael's portfolio companies like Tubular and Arbor against his stated focus in FinTech, teasing him about when his first FinTech deal will close.
Promotional Break: Austin Live Business Event and HostGator 0000 Mid-roll promotional ad break featuring host monologues for Austin Live and HostGator. No guest interaction or scoring dynamic.

Statements from this episode (3)

Assertion Not checkable as stated
Buddy Media and Vitrue Were the Last Major Social Assets in 2012
“Salesforce ended up running around and buying Buddy Media. And those are two very, very highly competitive processes. And those were kind of the last two assets in that space at the time.”
Michael Gilroy Jun 27, 2016 ▶ 3:14
Assertion Supported
Most VC Firms Do Not Start Hiring at the Analyst Level
“At Canaan, we started analysts and we go associate, then principal, then venture partner, then general partner. Most firms don't have an analyst role. It kind of starts at associates.”
Michael Gilroy Jun 27, 2016 ▶ 9:48
Opinion
David Einhorn Is One of the Sharpest, Most Thorough Investors
“Einhorn is a famous short seller for Greenlight Capital, one of one of the sharpest and most thorough investors you'll, you'll ever meet.”
Michael Gilroy Jun 27, 2016 ▶ 15:39
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