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

Summary Notes


In episode 26 of the 20 Minutes VC, host Harry Stebbings interviews Chris Redlitz, founding partner at Transmedia Capital, discussing his unconventional path from Reebok to pioneering in the digital space, including founding the first online Yellow Pages. Redlitz emphasizes the importance of investing in people over products, sharing insights from his experience with successful acquisitions by tech giants like Snapchat and LinkedIn. Additionally, Redlitz details his work with The Last Mile, a program he co-founded with his wife Beverly to teach technology and entrepreneurship to inmates at San Quentin, aiming to facilitate their reintegration into society. The program, which includes a rigorous coding curriculum, is set to scale nationally, with graduates potentially leading its expansion.

Summary Notes

Introduction to Chris Redlitz and The Last Mile Program

  • Chris Redlitz is a founding partner at Transmedia Capital.
  • Portfolio includes major tech companies like Snapchat, Twitter, Facebook, and LinkedIn.
  • Chris and his wife Beverly co-founded The Last Mile program in San Quentin prison in 2011.
  • The Last Mile helps prisoners build tech skills for post-incarceration employment.
  • Chris launched the first online Yellow Pages, automated coupon platform, and content syndication system.

"He is a founding partner at Transmedia Capital whose portfolio includes the likes of Snapchat, Twitter, Facebook and LinkedIn, just to name a few. Furthermore, in 2011, Chris and his wife Beverly, co co founded the last mile in San Quentin prison."

This quote introduces Chris Redlitz as a significant figure in the venture capital world and highlights his philanthropic work through The Last Mile.

Chris Redlitz's Entry into Venture Capital

  • Chris Redlitz took a nontraditional route into the VC world.
  • His background includes working for Reebok in the early 1980s during a period of significant growth.
  • He was part of the early internet era, starting with the online Yellow Pages.
  • Chris transitioned from working at Reebok to internet entrepreneurship, which led to his interest in investing.
  • He began investing in the mid-1990s and formalized his fund about six years before the podcast.

"I started investing in the mid 90s individually, and we formalized our fund almost six years ago."

Chris explains his progression from a career in sports and athletics to becoming an investor and eventually starting his own venture capital fund.

Key Determinants of Startup Success

  • Chris Redlitz discusses the crucial factors that contribute to a startup's success.
  • He mentions his involvement in competitive funding rounds for companies like Snapchat, Twitter, and LinkedIn.

"And Transmedia's portfolio includes the likes of Snapchat, Twitter, LinkedIn, and Angel list, just to name a few, leading me to ask, where do you personally believe are the crucial determinants of a startup's success, and how do you compete to be in such competitive rounds of funding?"

This quote sets up the question of what Chris believes are the essential elements for startup success and how he competes in high-stakes investment scenarios.

Investment Philosophy and Strategy

  • Chris Redlitz's investment focus is on early-stage companies and entrepreneurs, with a sector-specific approach targeting digital media, mobile commerce, and marketing automation platforms.
  • Redlitz emphasizes the importance of understanding the sectors in which he invests, adhering to a Warren Buffett-like philosophy.
  • A key factor in Redlitz's investment decisions is the quality of the people behind the companies, as he believes strong leadership can navigate through pivots in product and strategy.
  • His early investment in Josh James' company, which was later acquired by Adobe, exemplifies his people-over-product approach.
  • Redlitz's investment strategy has remained consistent over the years, with a focus on sectors he knows well and a belief in the enduring value of strong leadership teams.

"So that's how we have positioned those companies. We focused on very early stage, we focus primarily on the entrepreneur, but we're also somewhat sector specific where we invest in digital media, mobile commerce, marketing automation platforms, things like that. So we have more of a sector focus."

This quote summarizes Redlitz's investment approach, highlighting the emphasis on early-stage companies, entrepreneurial leadership, and a sector-specific focus.

"You have to really know what you're investing in, or else you shouldn't invest in it. And that's really what I've done. I stayed really in areas that I know well, but it really still about people."

Redlitz's quote underscores his investment philosophy, which involves a deep understanding of the sectors he invests in and prioritizing the people behind the companies.

Importance of People in Investments

  • Redlitz firmly believes that people are more important than the product when it comes to investment decisions.
  • He credits the success of his early investment in Josh James to James' leadership qualities and the retention of the founding team.
  • The ability of a strong team to persevere through changes in product and strategy is a recurring theme in Redlitz's investment strategy.

"People every time."

This succinct quote reflects Redlitz's conviction that the people behind a company are the most critical factor in his investment decisions.

"Companies will pivot in their product, in their strategy. But if you have a strong team, you can get through those times."

This quote emphasizes the value Redlitz places on leadership and the ability of a strong team to navigate through changes and challenges in the business.

Specialization in Digital Media

  • Redlitz's specialization in digital media originated from his experiences at Reebok, where he was involved in product placement, design, and promotions, particularly within the hip hop music scene.
  • His involvement in the online Yellow Pages further solidified his focus on media.
  • Redlitz recognized early on the potential for online platforms to disrupt traditional media, a prediction that has since been realized.

"I was involved in the online Yellow Pages, which sort of is a curferly in media, and I just kind of stuck with that."

The quote explains how Redlitz's early work with online Yellow Pages influenced his continued focus on the media sector.

"Saw the disruption pretty early on that online will disrupt traditional media. And obviously that's come true."

Here, Redlitz reflects on his foresight regarding the impact of online platforms on traditional media, reaffirming his sector specialization.

The Last Mile Program

  • The transcript does not provide details about The Last Mile program, as the speaker was interrupted before he could elaborate.

"Yeah, we started about five years ago, and I really had no background in prisons."

Although incomplete, this quote suggests that The Last Mile is a program that Redlitz co-founded about five years ago, unrelated to his prior experiences since he had no background in prisons.

Introduction to The Last Mile Program

  • The Last Mile is a program designed to teach entrepreneurship and coding to inmates in prison.
  • Chris Redlitz was inspired to start the program after a positive response from a talk he gave at San Quentin State Prison.
  • The program aims to provide inmates with tools to rebuild themselves.

"And I was invited in there to do a talk about entrepreneurship to a group of men, and I really didn't know if they would understand what I was talking about or be interested, but the response was so overwhelming that it really got me thinking about things that we do every day in the valley working with young entrepreneurs."

The quote explains the origins of The Last Mile program, which began after Chris Redlitz recognized inmates' interest in entrepreneurship during a talk he gave at San Quentin.

Tools Provided in The Last Mile Program

  • Inmates are given two types of educational tracks: entrepreneurship and coding.
  • The entrepreneurship track teaches inmates about changes in the world, especially technology, and how to build a business plan.
  • The coding curriculum includes learning CSS, HTML, and JavaScript.
  • The program is designed to be practical and includes a demo day where inmates present their business ideas to visitors, including venture capitalists.

"We teach them to build a business plan, they create that plan, and then we actually have a demo day inside the prison where they present their ideas."

This quote highlights the practical approach of the entrepreneurship track, culminating in a presentation of business plans to external visitors.

Structure and Intensity of The Last Mile Program

  • The entrepreneurship program involves sessions twice a week, each lasting three hours, with additional out-of-class work.
  • The coding program is more immersive, with inmates meeting Monday through Thursday for 10 hours a day.
  • Instruction for the coding program is provided virtually by Hack Reactor from San Francisco.

"In the coding side, it's very immersive. They are meeting Monday through Thursday, 10 hours a day."

This quote details the intensive nature of the coding track, indicating the commitment required by the inmates to learn new skills.

Scalability and Future Plans for The Last Mile Program

  • The coding program is designed for virtual instruction, which facilitates scalability to other prisons.
  • The program simulates a web environment for inmates to use without providing direct internet connectivity.
  • Plans are in place to expand the program to multiple prisons in the following year.

"But one of the reasons we did the virtual instruction is because we are going plan to go to multiple prisons and that's the best way to do it."

Chris Redlitz explains that virtual instruction was chosen to enable the program's expansion to more prisons, indicating the program's potential for national adoption.

Challenges in The Last Mile Program

  • The transcript ends before Chris Redlitz can elaborate on the challenges faced by The Last Mile program.

"And what's been the most challenging aspect of your journey with the last mile and how"

This incomplete quote suggests that challenges exist but does not provide details on the specific obstacles encountered during the implementation of The Last Mile program.

Working with Government Agencies

  • Chris Redlitz acknowledges the challenges of introducing innovation to legacy government agencies.
  • The startup mindset of rapid change clashes with the slower, methodical processes of government entities.
  • Patience and a methodical approach are essential when collaborating with government agencies.

I think it's working with government agencies not to say that they're resistant, but whenever you're doing something new and different, we're used to disruption, this whole idea of disruption in the startup environment, but when you're dealing with legacy agencies, that's something that's a little scary.

This quote underscores the inherent tension between the fast-paced, disruptive nature of startups and the cautious, established procedures of government agencies. Redlitz highlights the need for patience and education in navigating this relationship.

The Last Mile's Future

  • Chris Redlitz envisions The Last Mile expanding nationally within five years.
  • Graduates of the program are expected to take on leadership roles, allowing Redlitz to step back.
  • Empowering graduates to lead is a key goal for The Last Mile's future.

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.

Redlitz expresses his aspiration for growth and leadership transition within The Last Mile, indicating a strategic plan for scalability and sustainability by involving graduates in the program's future leadership.

Book Recommendations for Founders and VCs

  • Chris Redlitz recommends several books for aspiring founders and venture capitalists.
  • His top picks include "Losing My Virginity" by Richard Branson, "The Start-up of You" by Reid Hoffman, "Good to Great" by Jim Collins, and "Leadership Lessons from the Civil War."

Right in your neighborhood, losing your virginity by Richard Branson is a really good one. Startup of you by Reed Hoffman, and one that I actually give you two, I'm going to cheat. Good to great is always like the Bible. Absolutely. And leadership lessons from the Civil War is really kind of a unique one.

Redlitz offers a curated list of books that provide insights into entrepreneurship, personal development, business strategy, and historical leadership, reflecting a diverse set of resources for professional growth.

Recent Investments

  • Chris Redlitz discusses recent investments in a company called Nuco and an undisclosed startup.
  • He emphasizes the experience of Nuco's CEO, John Batel, and the technological proficiency of a "rock star CTO" at the other startup.
  • Redlitz values both experience and technical expertise in his investment decisions.

We actually have two that we've done recently. I think one was a company called Nuco. That's the CEO is John Batel, and John is very well known in media. He's done multiple startups, and it's really kind of a unique approach to conferences, creating festivals, and there's a lot of offshoot benefits to that. So he's a very experienced guy.

The quote highlights Redlitz's investment strategy, which includes a focus on the leadership's experience and the unique value proposition of the company, as exemplified by Nuco's innovative approach to conferences and festivals.

The Last Mile on Stanford's Entrepreneurial Thought Leaders Podcast

  • Harry Stebings promotes an interview with Chris Redlitz, his wife Beverly, and Horatio Hearts, a graduate of The Last Mile, on Stanford's Entrepreneurial Thought Leaders podcast.
  • The interview is described as inspirational and is accessible through the podcast's platform.

If you would like to hear more about the last mile, Chris and his wife Beverly did an incredible interview with an inspirational graduate of the program, Horatio Hearts, on Stanford's entrepreneurial thought Leaders podcast.

This quote serves as a pointer for listeners to gain further insights into The Last Mile and the impact it has on its graduates, through additional content provided by Stanford's podcast series.

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