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Apr 9, 2015 · 14m · 20vc

20 VC 026: Chris Redlitz on The Importance of People, Pivoting and The Last Mile

Chris Redlitz · 10m spoken Harry Stebbings · 3m 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 Transmedia Capital founding partner Chris Redlitz about his non-traditional journey into venture capital, his investment philosophy prioritizing founder leadership over initial product design, and his work co-founding The Last Mile coding program at San Quentin Prison.

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 24.6% of the talking time here. How this is scored →

Harry as informed peer 1.5 Guest teaching 2.3 Guest disagreement 0.3 Harry pushing back 0.5
05100:0010:001:13–3:14 · Harry as informed peer 1/10 Chris Redlitz's Background and Journey into Venture Capital Harry introduces Chris and asks an open-ended background question regarding his entry into VC. Chris provides a chronological summary of his career at Reebok and early internet startups without conflict or correction.3:15–6:03 · Harry as informed peer 3/10 Investment Strategy and Prioritizing People Over Product Harry names Transmedia's high-profile portfolio companies, but Chris gently clarifies that positions in Snapchat, Twitter, and LinkedIn resulted from acquisitions of portfolio startups like Scan and Snappy TV. Harry pushes Chris to choose between product and people, prompting Chris to emphasize team quality using Josh James as an example.6:04–10:04 · Harry as informed peer 1/10 Developing Expertise in Digital Media Harry asks about Chris's specialization in digital media and the origin of The Last Mile program at San Quentin. Chris elaborates on the entrepreneurship and coding tracks, maintaining a purely informational and collaborative exchange.10:04–11:50 · Harry as informed peer 1/10 Scaling The Last Mile and Navigating Government Bureaucracy Harry asks how Chris plans to scale the program nationally and what challenges he faces. Chris details their virtual instruction setup and the need for patience when dealing with legacy government agencies.1:13–3:14 · Guest teaching 1/10 Chris Redlitz's Background and Journey into Venture Capital Harry introduces Chris and asks an open-ended background question regarding his entry into VC. Chris provides a chronological summary of his career at Reebok and early internet startups without conflict or correction.3:15–6:03 · Guest teaching 4/10 Investment Strategy and Prioritizing People Over Product Harry names Transmedia's high-profile portfolio companies, but Chris gently clarifies that positions in Snapchat, Twitter, and LinkedIn resulted from acquisitions of portfolio startups like Scan and Snappy TV. Harry pushes Chris to choose between product and people, prompting Chris to emphasize team quality using Josh James as an example.6:04–10:04 · Guest teaching 2/10 Developing Expertise in Digital Media Harry asks about Chris's specialization in digital media and the origin of The Last Mile program at San Quentin. Chris elaborates on the entrepreneurship and coding tracks, maintaining a purely informational and collaborative exchange.10:04–11:50 · Guest teaching 2/10 Scaling The Last Mile and Navigating Government Bureaucracy Harry asks how Chris plans to scale the program nationally and what challenges he faces. Chris details their virtual instruction setup and the need for patience when dealing with legacy government agencies.1:13–3:14 · Guest disagreement 0/10 Chris Redlitz's Background and Journey into Venture Capital Harry introduces Chris and asks an open-ended background question regarding his entry into VC. Chris provides a chronological summary of his career at Reebok and early internet startups without conflict or correction.3:15–6:03 · Guest disagreement 1/10 Investment Strategy and Prioritizing People Over Product Harry names Transmedia's high-profile portfolio companies, but Chris gently clarifies that positions in Snapchat, Twitter, and LinkedIn resulted from acquisitions of portfolio startups like Scan and Snappy TV. Harry pushes Chris to choose between product and people, prompting Chris to emphasize team quality using Josh James as an example.6:04–10:04 · Guest disagreement 0/10 Developing Expertise in Digital Media Harry asks about Chris's specialization in digital media and the origin of The Last Mile program at San Quentin. Chris elaborates on the entrepreneurship and coding tracks, maintaining a purely informational and collaborative exchange.10:04–11:50 · Guest disagreement 0/10 Scaling The Last Mile and Navigating Government Bureaucracy Harry asks how Chris plans to scale the program nationally and what challenges he faces. Chris details their virtual instruction setup and the need for patience when dealing with legacy government agencies.1:13–3:14 · Harry pushing back 0/10 Chris Redlitz's Background and Journey into Venture Capital Harry introduces Chris and asks an open-ended background question regarding his entry into VC. Chris provides a chronological summary of his career at Reebok and early internet startups without conflict or correction.3:15–6:03 · Harry pushing back 2/10 Investment Strategy and Prioritizing People Over Product Harry names Transmedia's high-profile portfolio companies, but Chris gently clarifies that positions in Snapchat, Twitter, and LinkedIn resulted from acquisitions of portfolio startups like Scan and Snappy TV. Harry pushes Chris to choose between product and people, prompting Chris to emphasize team quality using Josh James as an example.6:04–10:04 · Harry pushing back 0/10 Developing Expertise in Digital Media Harry asks about Chris's specialization in digital media and the origin of The Last Mile program at San Quentin. Chris elaborates on the entrepreneurship and coding tracks, maintaining a purely informational and collaborative exchange.10:04–11:50 · Harry pushing back 0/10 Scaling The Last Mile and Navigating Government Bureaucracy Harry asks how Chris plans to scale the program nationally and what challenges he faces. Chris details their virtual instruction setup and the need for patience when dealing with legacy government agencies.

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

0:00 · Harry 46.9% · guest 53.1%0:00 · Harry 46.9% · guest 53.1%3:00 · Harry 20% · guest 80%3:00 · Harry 20% · guest 80%6:00 · Harry 12.9% · guest 87.1%6:00 · Harry 12.9% · guest 87.1%9:00 · Harry 14.8% · guest 85.2%9:00 · Harry 14.8% · guest 85.2%12:00 · Harry 29.4% · guest 70.6%12:00 · Harry 29.4% · guest 70.6%
Sharpest disagreement ▶ 3:35 Polite clarification on portfolio positions

Chris mildly resists the premise that Transmedia directly backed giant tech firms by explaining that positions in Snapchat, Twitter, and LinkedIn came through M&A deals.

 Hardest push from Harry ▶ 4:10 Forcing a choice between product and people

Harry pushes Chris to commit to a binary priority by asking whether product or people matters more in early-stage success.

 Biggest teaching moment ▶ 3:35 Explaining acquisition mechanics

Chris educates Harry on how Transmedia obtained equity in major platforms by listing the original seed-stage companies they backed, such as Scan and Snappy TV.

 Harry holds his own ▶ 3:14 Demonstrating portfolio research

Harry showcases background research on Transmedia's portfolio investments to frame his inquiry into competitive deal dynamics.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Chris Redlitz's Background and Journey into Venture Capital 1100 Harry introduces Chris and asks an open-ended background question regarding his entry into VC. Chris provides a chronological summary of his career at Reebok and early internet startups without conflict or correction.
Investment Strategy and Prioritizing People Over Product 3412 Harry names Transmedia's high-profile portfolio companies, but Chris gently clarifies that positions in Snapchat, Twitter, and LinkedIn resulted from acquisitions of portfolio startups like Scan and Snappy TV. Harry pushes Chris to choose between product and people, prompting Chris to emphasize team quality using Josh James as an example.
Developing Expertise in Digital Media 1200 Harry asks about Chris's specialization in digital media and the origin of The Last Mile program at San Quentin. Chris elaborates on the entrepreneurship and coding tracks, maintaining a purely informational and collaborative exchange.
Scaling The Last Mile and Navigating Government Bureaucracy 1200 Harry asks how Chris plans to scale the program nationally and what challenges he faces. Chris details their virtual instruction setup and the need for patience when dealing with legacy government agencies.

Statements from this episode (8)

Assertion Partly supported
Reebok was doing $10M-$12M in sales when Chris Redlitz joined
“I joined the company very, very early on in the early eighties when the company was doing, you know, just I think we were doing about 10 to twelve million dollars in sales.”
Chris Redlitz Apr 9, 2015 ▶ 1:48
Disclosure
Transmedia Capital gained Snapchat, Twitter, and LinkedIn stakes via startup acquisitions
“Well, those Snapchat, LinkedIn, and Twitter were all through acquisitions. Scan was a company that was acquired by Snapchat. Snappy TV was acquired by Twitter, and Nozzle was acquired by LinkedIn. So that's how we have positions those companies.”
Chris Redlitz Apr 9, 2015 ▶ 3:37
Disclosure
Transmedia Capital invested in Josh James's startup Domo
“And now he has a company called Domo, which we're all, all also invested in, which is doing extremely well.”
Chris Redlitz Apr 9, 2015 ▶ 5:48
Assertion Contradicted
The Last Mile launched the first prison coding program in the US
“And we also, this past year, started a coding curriculum where the guys learn CSS, HTML, and JavaScript, and it's the first coding program in the country in a U.S. Presentation.”
Chris Redlitz Apr 9, 2015 ▶ 8:55
Assertion Not checkable as stated
Half of San Quentin coding students had never touched a computer
“I think half the class had never touched a computer, and no one certainly had done any coding, and they're doing extremely well.”
Chris Redlitz Apr 9, 2015 ▶ 9:46
Assertion Supported
The Last Mile created a simulated web for secure prison coding instruction
“For the coding side, we actually built it out so that it is virtual, so we do the instruction from San Francisco and do a feed into the prison. And we actually, our instructor inside also has connectivity. None of the guys have locally, to their local machine,…”
Chris Redlitz Apr 9, 2015 ▶ 10:05
Prediction Held up
Chris Redlitz predicts The Last Mile will expand nationally by 2020
“I see it national, and I see many of the guys that are graduates actually running the program, and I see myself stepping back a bit. Not that I don't want to be involved, but I want to give the guys in the program a chance to really step up and lead.”
Chris Redlitz Apr 9, 2015 ▶ 12:05
Disclosure
Transmedia Capital recently invested in John Battelle's NewCo
“We actually have two that we've done recently. You know, I think one was a company called Nuko that's CEO is John Battell, and John is very, very well-known in media.”
Chris Redlitz Apr 9, 2015 ▶ 13:04
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