Sep 6, 2021 · 1h 14m · how-i-built-this
Lynda.com: Lynda Weinman and Bruce Heavin
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 'How I Built This,' host Guy Raz interviews Lynda Weinman and Bruce Heavin, tracing their journey from pioneering digital design educators to building Lynda.com into a subscription video powerhouse that sold to LinkedIn for $1.5 billion.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 33.6% of the talking time here. How this is scored →
Guy as informed peer 3.3 Guest teaching 2.4 Guest disagreement 1.1 Guy pushing back 0.5
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 54:11 Lynda entirely dismisses major competitor Skillsoft
When Guy brings up industry leader Skillsoft, Lynda outright rejects the premise that they were meaningful rivals, declaring Skillsoft lacked her respect, envy, or attention.
Hardest push from Guy ▶ 41:09 Guy challenges the decision to cannibalize physical salesGuy incredulously challenges whether anyone in the company pushed back against selling unlimited digital streaming for $25 a month while selling physical tapes for $150.
Biggest teaching moment ▶ 43:54 Bruce educates host on closed captioning SEO vs. broadcast marketingBruce corrects Guy's assumption about marketing driving growth by detailing how organic enterprise adoption and video closed-caption metadata were far more impactful than traditional media.
Guy holds their own ▶ 14:09 Guy details early Macintosh graphical computing breakthroughGuy articulately contextualizes the revolutionary technological shift from command-line computing to graphical user interfaces and mice for the listener.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Lynda's Childhood and Developing Hyper-Responsibility | 2 | 1 | 1 | 0 | Guy invites Lynda to share personal reflections on her childhood and family dynamics. Lynda speaks candidly about feeling unwanted yet loved and how that shaped her hyper-responsibility. | |
| Alternative Education at Sherwood Oaks High School | 4 | 2 | 1 | 1 | Guy tracks Lynda's journey through Sherwood Oaks and her early retail venture Vertigo, citing specific details like its punk aesthetic and location. Lynda corrects the nostalgia around her high school and recounts the failure of her store. | |
| Transitioning to Film Animation and Rotoscoping | 3 | 2 | 0 | 0 | Guy brings historical context regarding early Apple Mac interfaces versus command line systems. Lynda details how rotoscoping work and asking for community help allowed her to master early 3D software. | |
| Teaching at Art Center, Buying Lynda.com, and Publishing | 3 | 3 | 1 | 0 | Guy inquires about her early web design teaching and domain acquisition. Lynda explains how she noticed web graphics were ignored by technical authors, driving her to write the seminal book and buy lynda.com. | |
| Bruce Heavin's Perspective and Their Early Relationship | 2 | 1 | 1 | 0 | Guy introduces Bruce Heavin to the conversation and explores their initial classroom dynamic and subsequent romance. Both guests share humorous, affectionate memories of meeting and reconnecting. | |
| Founding the In-Person School in Ojai | 3 | 2 | 1 | 0 | Guy explores the transition to running in-person workshops in Ojai. Lynda admits she was initially resistant to Bruce's business ideas due to fear of failure, but high international demand proved him right. | |
| Expanding into Instructional Video Production on VHS | 4 | 3 | 2 | 1 | Guy asks how they financed video production and handled distribution. Bruce politely corrects Lynda on the initial sponsorship dollar amount, and both recount their low-tech mail-order operations. | |
| The Impact of the Dot-Com Crash and September 11 | 4 | 2 | 1 | 0 | Guy asks about the dual impact of 9/11 and the dot-com crash on their in-person school. Lynda explains the severe financial strain of bootstrapping through the crisis and the pain of letting staff go. | |
| Launching the $25/Month Digital Subscription Service | 4 | 3 | 1 | 2 | Guy questions whether moving online in 2001 made sense given dial-up internet and asks if offering $25/month access cannibalized their $150 VHS sales. Lynda and Bruce confirm it initially hurt revenue but set up their long-term digital model. | |
| Broadband Adoption, SEO, and Educational Differentiation | 3 | 4 | 2 | 1 | Guy suggests paid advertising or marketing drove their resurgence. Bruce and Lynda reframe this, explaining that marketing and even Howard Stern mentions yielded little, whereas closed captioning SEO and word-of-mouth fueled adoption. | |
| Professionalizing Leadership and Scaling to Carpinteria | 4 | 3 | 1 | 1 | Guy asks why the founders chose to hire outside CEO Eric Robison when reaching eight figures. Lynda explains their awareness of their own operational limits and how Robison advised them to professionalize rather than take early VC money. | |
| Reaching $100 Million and Intuitive Trend Forecasting | 4 | 4 | 2 | 1 | Guy brings up competitor Skillsoft to ask about market dynamics. Lynda dismisses Skillsoft as irrelevant to her radar, while Bruce pushes back against relying solely on data analytics in favor of intuitive trend forecasting. | |
| The Pitfalls of Venture Capital and Loss of Control | 4 | 3 | 2 | 1 | Guy presses on why they accepted a $100M venture round after bootstrapping for decades. Lynda and Bruce reveal internal disagreements, the loss of cultural control to investor pressure, and the personal burnout that resulted. | |
| The $1.5 Billion Acquisition by LinkedIn | 4 | 2 | 1 | 0 | Guy reviews the rapid $1.5 billion acquisition by LinkedIn. Bruce and Lynda describe the whirlwind two-month negotiation and the sudden, disorienting loss of their workplace community after closing. | |
| Life After Lynda.com, Wealth, and Philanthropy | 2 | 1 | 0 | 0 | Guy asks how substantial wealth altered their day-to-day lives and happiness. Lynda quotes Will Smith regarding wealth as an accelerant of character, and Bruce notes his happiness remains rooted in making things. | |
| Reflections on Success, Luck, and the 'Story of No' | 3 | 3 | 1 | 0 | Guy closes with his signature luck vs. skill question. Lynda attributes 25% to luck, while Bruce reframes their success around overcoming barriers in what he calls the 'story of no.' |
Statements from this episode (27)
ZZ Top bought 1,000 Ray-Bans from Lynda Weinman's early boutique
“I had ZZ Top buy, like, a thousand Ray-Ban sunglasses for me one time to give out at concerts.”
Lynda Weinman bought the first Apple Macintosh for $2,500 on credit
“I bought it at a, with my May Company credit card for 2500 dollars for the very first Mac, which if I had saved it would be worth, you know, fortune today.”
Weinman created Star Trek Mac animatics directly for William Shatner
“I had an assignment to do animatics, an animated storyboard on a Mac, and I worked directly with William Shatner on One of the Star Trek movies, and I had never done anything like that, and I had to build the Starship Enterprise, and I had no idea how to build…”
Lynda Weinman purchased the lynda.com domain name for just $35
“And sure enough, it was for 35 dollars, so I bought it.”
Weinman: Lynda.com reached top 100 global websites by web traffic
“There were times where we would look at where we ranked in the world in terms of traffic, and we would be in the top 100 websites in the world, you know, because we were just so early.”
Weinman: web design book became the best-selling in the world
“And it was, at the time, the best-selling web design book in the world, used at every college.”
Bruce Heavin: Adobe and Martha Stewart sent employees to Lynda.com workshops
“And we were having Adobe sending their employees to us. Martha Stewart was sending employees to us.”
Lynda.com generated $1.7 million in revenue in its first year
“In the first year, our revenue was 1.7 million dollars, which to us was just, you know, we'd never imagined.”
Early Lynda.com sold video tapes via mail-in checks without e-commerce
“We had no e-commerce. We had a thing on the website that said, send your check and money order to PO Box in Ojai, California, and then we had notified them by email when we got their payment. So people were sending their checks and money orders to our PO Box i…”
Weinman: Lynda.com was 100% bootstrapped without investor funding
“We had never taken investor money at all. It never, we never, even that word startup just wasn't in the vernacular at that point. I mean, we were really old school. This was a bootstrapped business, 100%.”
Weinman: Lynda.com laid off over half its workforce in 2001
“We had to lay off more than half our people.”
Weinman: Offering free content is the enemy of a successful business
“You know, we sort of felt that free was the enemy of a successful business.”
Lynda.com dipped to $1M in revenue and 9 employees at its low point
“Even the year, I think our worst year, We did a little over one million dollars in the year and we had like nine employees.”
Lynda.com secured massive enterprise adoption entirely through organic employee demand
“A lot of people who taught web design and Photoshop were using our courses, and they were bringing it into their schools and into their companies, so we'd be installed in all of Apple, all of Adobe, all of Microsoft, all of Google, and the employees were start…”
Adding closed captioning drove more growth for Lynda.com than paid marketing
“Believe it or not, it, the closed captioning was a very beneficial thing to us, more so than any marketing.”
Weinman: Lynda.com dropped books, DVDs, and classes to go all-in online
“We had sort of this moment of reckoning right around 2005, 2006, and it was, what do we do that's different from all the competitors in the field? What's our differentiator? And we made the decision. It's the fact that we're delivering online and that's our co…”
Inbound investor interest in Lynda.com surged at $10 million in revenue
“I remember when we hit this sort of magic number, ten million in revenue, that the phone started ringing off the hook with people wanting to invest in us.”
Weinman: Scale New Topics by Empowering Connected Domain Insiders to Curate Instructors
“So what you do is you find another me, you find somebody who is an industry insider at the top of their field, who knows everybody. And then they were empowered to, you know, curate who they were going to invite to come in as teachers and oversee the quality o…”
Weinman: Competitor Skillsoft did not have my respect, envy, or attention
“I never really thought about them as a competitor, to be honest. They weren't even really on my radar. I did, they didn't have my respect. They didn't have my envy. They didn't have my attention.”
Heavin: Data analytics cannot successfully drive educational content programming
“You can't do all this based on data analytics to understand what you need to do for programming of content for learning. But I kind of always had this belief you had to be a little bit of a bookie and a fortune teller. And the data analytics is very important,…”
Heavin: Taking venture capital starts a clock and shifts employee motives
“I knew the second you take a dime, we're starting a clock. We're starting expectations. It kind of changes the nature of people when they even come for a job interview. You know, the question is, how much stock do I get, you know?”
Weinman realized her hired CEO held more power than the founders
“And I realized very late in the game that the CEO had more power than I did. And more power than Bruce did.”
Venture capital shifted Lynda.com to merciless EBITDA optimization
“And I think my fear was realized because it took away our passion and focus on education, and it drove it down Just a pure business path, and decisions were merciless. It was just about how to gain EBITDA, and it made working there a lot less fun.”
Heavin: Employee departures surged at Lynda.com after raising venture capital
“It made working there a lot less interesting, and I could tell you I could count on one hand how many people chose to leave before we took money. But after we took money and the business started changing because of investors, because of this pressure, we had m…”
Weinman: LinkedIn Was the Perfect Suitor for Lynda.com
“It was not, it didn't feel perfect at the time, but it was the perfect suitor with the perfect business and the perfect time, and even though, you know, they've done something different with it than what we were doing, I know it's been super successful for the…”