Nov 11, 2019 · 1h 3m · how-i-built-this
Evite: Selina Tobaccowala
Selina Tobaccowala · 37m spoken Guy Raz · 17m spoken Jamia Ramsey · 1m spoken Ramtin Arablouei · 12s spoken Rund Abdelfatah · 6s spoken
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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 entrepreneur Selina Tobaccowala about co-founding Evite, surviving the dot-com crash, and evolving into a seasoned Silicon Valley executive and serial founder.
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 32.3% of the talking time here. How this is scored →
Guy as informed peer 3.8 Guest teaching 2.2 Guest disagreement 0.3 Guy pushing back 0.7
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 56:06 Reframing Luck as Privilege
Tobaccowala rejects the standard dichotomy of luck versus hard work, correcting Raz to emphasize that what many label luck is actually structural privilege.
Hardest push from Guy ▶ 41:57 Challenging the Necessity of Selling EviteRaz presses Tobaccowala on why Evite was forced into a fire sale rather than continuing to operate independently with a lean staff post-layoffs.
Biggest teaching moment ▶ 37:20 Educating on VC Incentives in Market Down turnsTobaccowala provides a candid breakdown of how institutional VCs prioritize quick capital recovery and fund-level multiples over company preservation.
Guy holds their own ▶ 34:51 Contextualizing Early Dot-Com Advertising MetricsRaz demonstrates strong historical fluency in early web economics, challenging the assumptions around banner ad pricing and digital runway before the collapse.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Childhood Coding, Paternal Mentorship, and High School Achievements | 4 | 2 | 0 | 1 | Guy asks background questions about Tobaccowala's childhood interest in computers, while she details how her father's work at EDS inspired her early programming. | |
| Stanford Experience, Early Web Days, and Meeting Al Lieb | 5 | 1 | 0 | 0 | Raz contextualizes the early 1994 internet landscape including Netscape's launch, and Tobaccowala describes freshman life at Stanford meeting Al Lieb. | |
| Academic Doubts, Wall Street Internship, and Berlin Reunion | 3 | 2 | 0 | 0 | Tobaccowala shares her early crisis of confidence in CS, her summer banking IT internship, and returning from Berlin to co-found a company with Lieb. | |
| Experimenting with OodleWorks and Designing the Collage Portal | 3 | 2 | 0 | 0 | The conversation covers their failed first idea OodleWorks and their subsequent creation of Collage, an early personalized web portal. | |
| Building on a Budget and Pitching Collage to Excite | 4 | 3 | 1 | 1 | Raz asks how undergrads could secure meetings with high-level tech executives, and Tobaccowala directly attributes it to the unearned privilege of the Stanford network. | |
| Pondering Career Choices and Paternal Advice on Startup Risk | 4 | 4 | 1 | 2 | Raz inquires about the $50,000 licensing agreement with Excite, and Tobaccowala corrects his assumption that they were handed cash immediately, clarifying the harsh exclusivity terms and delayed payment. | |
| From Enterprise Scheduling to Consumer Events: The Evite Pivot | 4 | 2 | 0 | 0 | Tobaccowala explains how enterprise resistance to cloud calendaring pushed them to pivot directly to consumer-facing event invitations. | |
| Launching Evite, Inherent Virality, and the Consumer Internet Wave | 5 | 2 | 0 | 0 | Raz and Tobaccowala discuss the mechanics of organic viral loops before the terminology existed, alongside the cultural shift away from paper invitations. | |
| Hiring CEO Josh Silverman and Raising Millions in Capital | 5 | 3 | 0 | 1 | Raz presses on the late-90s venture mania where revenue was ignored in favor of pure pageviews, which Tobaccowala confirms from her board experiences. | |
| San Francisco Scaling, Brand Sponsorships, and Market Reversal | 5 | 2 | 0 | 2 | Raz probes the burn rate and lack of profitability despite big brand sponsorships right before the sudden dot-com crash. | |
| Mid-Show Break: The Impending Crash and Recap | 4 | 4 | 1 | 1 | Tobaccowala breaks down the harsh reality of venture fund economics during a crash, recounting the traumatic layoff of over half their staff. | |
| Evite Acquisition by Ticketmaster CitySearch and Relocation | 4 | 3 | 0 | 2 | Raz questions why Evite had to sell instead of staying lean, and Tobaccowala explains that founder control had been lost to investors requiring a liquidity exit. | |
| Transitioning to Corporate Management at Ticketmaster | 3 | 1 | 0 | 0 | Tobaccowala describes adjusting to corporate life as an employee at Ticketmaster CitySearch after years as an autonomous founder. | |
| Joining SurveyMonkey and Mentorship Under Dave Goldberg | 3 | 2 | 0 | 0 | Tobaccowala details her move to SurveyMonkey, her mentorship under Dave Goldberg, and negotiating executive equity while disclosing her pregnancy. | |
| Coping with Loss, Pivoting to Wellness, and Founding Gixo | 3 | 1 | 0 | 0 | Following Goldberg's tragic death, Tobaccowala re-evaluates her priorities and reunites with Lieb to bootstrap fitness startup Gixo. | |
| Executive Leadership, the Impact of Privilege, and Evite's Legacy | 5 | 4 | 2 | 1 | When Raz introduces the standard 'luck vs. skill' dilemma, Tobaccowala reframes luck as systemic socioeconomic privilege. | |
| NPR Promo: Throughline History Podcast | 0 | 0 | 0 | 0 | Promotional clip for NPR's Throughline podcast followed by the 'How You Built That' segment featuring Jamia Ramsey of Blends. |
Statements from this episode (19)
Tobaccowala: Berlin Had No Tech Scene in Late 1990s
“There's so much going on in Silicon Valley. There's no technology going on in Berlin.”
Tobaccowala: Collage conceived personalized web homepages before My Yahoo
“And the idea was, is that you could clip together stuff from all over the web, create your own homepage, and then algorithmically, we would update it for you as things updated. And this was before my Yahoo, before that concept of creating a homepage.”
Tobaccowala: Stanford Network Gives Founders Privilege to Secure Executive Meetings
“That is the beauty of the Stanford network. You know, these are the things that, that you can't discount when you think about privilege that people have. It's like, you reach out to, you know, an executive at Excite and their executive at Yahoo, and you say, I…”
Tobaccowala: Early Startup Signed Exclusive Tech License With Excite
“We licensed our technology and product to them exclusively, so we gave them this huge window of time that they had exclusivity, and that meant we couldn't actually go work with slash sell it to anybody else in that time frame.”
Tobaccowala: Evite Conceived in 1998 as Consumer Adaptation of Web Calendar
“We're sitting outside, and we said, oh, well, what if we take this web calendar thing and we let consumers do it? Let them organize stuff with their friends. And that was the birth of Evite, and this was July, August, 1998.”
Tobaccowala: Email Invites Must Withhold Full Details to Drive Clicks
“One of the learnings we had was you couldn't put the information in the email because then nobody would click through. So we put enough information in the email to entice you, and then you would click through, and you would come to this page, to RSVP.”
Tobaccowala: Each Evite Sent Reached an Average of 18 People
“With the way that Evite was designed, by nature, as soon as you send one, there was an average of 18 other people that found out about it, and then one of those people just had to say, oh, this is interesting, I'm gonna go ahead and create an Evite, and then t…”
Tobaccowala: Evite Raised First $5.7M Financing From August Capital
“And we raised our first financing around 5.7 million dollars from August capital.”
Tobaccowala: Evite Raised $37M Total for Online Invitations in 1999
“We raised thirty-seven million dollars for online invitations.”
Tobaccowala: 1999 VCs Focused Entirely on Eyeballs Rather Than Revenue
“All of the venture capitalists at the time, they were focused on this metric eyeballs. How many eyeballs do you have? How many? And that meant like how many people are actually visiting your site? What's your growth in terms of actual, just unique visitors? Th…”
Tobaccowala: Evite Reached at Least 1M Users in First Year
“In the first year, we had at least a million users using the product.”
Tobaccowala: Evite was nowhere near profitable with 75 employees around 2000
“Even though we had some of these big brands, we were starting to see some revenue, but no way were we close to profitability. And you suddenly have 70, 75 people on your operating expense.”
Tobaccowala: Dot-com focus shifted abruptly from traffic to profitability in mid-2000
“Everything was about, like, you know, the growth and the traffic, and there was no discussion or talk about revenue. And then the bubble burst, and all of a sudden, all anybody could I could talk about was, oh my gosh, all these companies are bleeding money. H…”
Tobaccowala: Evite's Wall Street Journal sale ad attracted multiple buyers
“Yeah, we knew people loved the brand, and people recognized the brand, and so we said, look, like, let's put it out there, and let's do something bold, and we did, and that did bring multiple buyers to the table.”
Tobaccowala: VCs Forced Evite Sale After Dot-Com Crash Erased Valuations
“We definitely could have continued with a thinner staff, but the main concern was from the venture capitalists in the sense that they are looking at, can this become a billion-dollar valued business? And given that, all of a sudden, valuations had fallen throu…”
Tobaccowala: Only two employees transitioned in Ticketmaster Evite acquisition
“So actually only two of us went with the deal. Myself and this other guy, Jim, who was in charge of all of the advertising relationships. And so we were literally moving the company down to LA, and we were going to rebuild.”