Dec 2, 2020 · 32m · we-live-to-build
The Truth About Patents: 'I Did Everything Right — It Hurt Me'
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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 We Live to Build, host Sean Weisbrot interviews Cheekt founder Lori Cheek about her transition from architecture to tech entrepreneurship, detailing the realities of bootstrapping, viral marketing, Shark Tank rejection, and surviving multi-million-dollar patent lawsuits.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Sean holds 41.9% of the talking time here. How this is scored →
Sean as informed peer 3.7 Guest teaching 1.2 Guest disagreement 0.7 Sean pushing back 0.7
speaking balance: gold is Sean, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 28:23 Refusing cynical takeaways on Shark Tank and patents
When Sean suggests the moral of the story is never to file patents or go on Shark Tank, Lori firmly rejects this framing, asserting that she would do it all over again because of the positive inspiration and career opportunities it generated.
Hardest push from Sean ▶ 13:52 Calling out street card scraping as bad practiceAfter Lori confesses to picking up random business cards off the sidewalk to populate her startup's mailing list, Sean blunt cuts in to criticize and reject the tactic as bad practice.
Biggest teaching moment ▶ 27:16 Educating the host on how IP protection backfiredLori dismantles conventional founder wisdom by explaining that doing everything legally right—filing trademarks, copyrights, and patents—actually made her an easy target for opportunistic multimillion-dollar lawsuits.
Sean holds their own ▶ 23:48 Contextualizing COVID timelines using historical precedentSean demonstrates historical analytical expertise by breaking down the 1918-1920 Spanish flu cycle to accurately project government pandemic responses and business implications.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Sean as informed peer | Guest teaching | Guest disagreement | Sean pushing back | Why |
|---|---|---|---|---|---|---|
| Transitioning from Architecture to Founding Cheekt | 3 | 2 | 1 | 1 | Sean compares Cheekd to Tinder, prompting Lori to explain how her concept pre-dated widespread smartphone apps and focused on real-world serendipity. Sean validates this context by sharing his own recollections of early social media and college communication. | |
| Bootstrapping, Entrepreneurial Risk, and Career Shifts | 4 | 1 | 0 | 0 | Lori reflects on investing her personal savings into her startup as an informal MBA. Sean takes over with a lengthy analysis comparing entrepreneurial risk tolerance to his brother's career and wealth cycles, which Lori fully agrees with. | |
| Early Startup Mistakes and Non-Technical Founder Lessons | 4 | 1 | 0 | 0 | Lori recounts her major early mistake of splitting 30% equity between two partners with identical non-technical skillsets. Sean relates his own startup experience hiring a lead developer to serve as an interim technical evaluator. | |
| Guerrilla Marketing Tactics and Early Media Sensations | 4 | 1 | 1 | 2 | Lori describes getting viral press in the New York Times and admitting she grabbed business cards off street pavement to harvest leads. Sean details his own multi-channel grassroots PR funnel and playfully scolds her street-card tactic as bad practice. | |
| Development Disasters and Costly Technology Pitfalls | 4 | 1 | 0 | 0 | Lori shares a costly technical disaster where a developer failed to save customer credit card credentials, costing $30,000. Sean sympathizes by detailing his own experience firing an insubordinate backend developer who ignored architectural documentation. | |
| The Shark Tank Experience and Pitch Rejection | 2 | 1 | 1 | 0 | Lori details the intense psychological pressure of taping Shark Tank, freezing on set, and being rejected harshly by Mark Cuban and Kevin O'Leary. Sean serves purely as an inquisitive listener exploring the emotional and editing reality of television. | |
| Post-Shark Tank Aftermath and Pivoting During COVID-19 | 5 | 1 | 0 | 1 | Lori discusses post-show reinvention and how the pandemic crippled in-person dating apps. Sean demonstrates domain expertise by citing the 1918 Spanish flu historical trajectory and advising Lori to steer completely clear of virtual reality headsets. | |
| The Reality of Patent Lawsuits and Legal Battles | 4 | 2 | 3 | 2 | Lori explains how a frivolous multivariable patent lawsuit cost her years of legal grief despite doing everything by the book. Sean proposes cynical takeaways (avoiding US incorporation and patents), but Lori pushes back, stating she would still do it again for the platform and resilience it created. | |
| Maintaining Mental and Physical Wellness as a Founder | 3 | 1 | 0 | 0 | The conversation turns to founder wellness and stress mitigation, where Lori shares her daily cycling routine in Kentucky. Sean complements her routine with his own 16-year meditation and joint mobilization practices before wrapping up. |
Statements from this episode (11)
Cheek says in-person encounters prevent the profile masking common on Tinder.
“Well, you know, on Tinder, you can be anybody you want to be, but when you see somebody in person, there's no masking that on a picture because you've already seen them in real life.”
Cheek funded the launch of Cheek'd using her personal retirement savings.
“I used my little piggy bank... This money that I'd saved was for retirement, it was for my future, but when I came up with this idea, I thought, you know, I'm gonna invest all this money into me, and this is gonna turn into billions.”
Cheek regrets giving 30% equity to two partners with identical skill sets.
“Ok, so I gave these two guys 30% equity in my business. Those two guys had the same skill set. Why did I need a clone that I'm just giving 15% equity to both of these people?”
Cheek landed on the New York Times cover by mailing one card.
“I remember I sent a lone cheeked card, one of those cards I invented, and a black padded envelope to one of the editors of the New York Times. Three months later, we're on the cover of the style section of the New York Times, and it said moveovermatch.com. Thi…”
Weisbrot uses podcast guest invitations as a startup lead generation funnel.
“Part of the podcast is meant to drive traffic back to this whole thing. So when I go to people and I say, Hey, I'm doing a podcast. I'm interested in talking to you about, you know, you being a guest. Oh, and you know, tell me about your company. And then when…”
Cheek built an early database using discarded business cards found on streets.
“I'm probably going to get sued for saying this, but I used to pick up business cards off the street in New York city and add them to my database.”
A developer error cost Cheek'd $30,000 during its New York Times spike.
“That developer in London had that button ticked off that didn't save everyone's credit card. So we lost every single person's credit card from that push from the New York Times, which based on our average monthly user, that turned out to be about 30,000 dollar…”
All five Shark Tank investors rejected Cheek's pitch for Cheek'd.
“I got shot down by all five of them, and I remember standing there thinking, I can't just walk off with this rejection, so I pointed at each of them, and I said, trust you will all see me again, and then I turned around and walked off, but they cut that on the…”
Cheek'd pivoted to a Bluetooth dating app with a 30-foot radius.
“So I took Barbara Corcoran's advice, pivoted the idea, and now we have a Bluetooth dating app minus the cards. So you connect in person and unlike Tinder, you can see the person within a 30 foot radius and then swipe on them.”
Cheek argues that securing patents and trademarks ultimately hurt her business.
“I did the trademark, the patent, the copywriting, everything to protect my idea. But in fact, all of that that I did, it went the opposite way. I think it ended up hurting me because this man is trying to get on my patent, which I don't even think is worth any…”