Learnings from the acqui-hire of a travel startup

We had the chance to speak with Eric Shepard, formerly of Trill Travel.  Trill had a successful acqui-hire exit to Lonely Planet.  Eric shared his story with us; lessons from his experience are below.


What was TRILL? TRILL is an artificial intelligence-driven travel marketplace that turns Instagram posts into bookable experiences. TRILL’s dual-sided marketplace gives content creators $30 cash every time someone books a hotel through their content.  As opposed to a  traditional booking site, consumers had the ability to plan and book trips through a different lens – beautiful, trending Instagram content.


Accelerator wasn’t helpful.  TRILL got into an accelerator called Plug & Play which was travel focused and based in San Francisco.  Overall, Eric didn’t get that much value from the accelerator.  That particular program seemed more geared towards its corporate partners than helping grow entrepreneurs.  It was great exposure but wasn’t as valuable for Eric because he was earlier stage.  Eric felt it was more valuable for later stage companies for future partnerships and investment opportunities.  They didn’t provide capital but they don’t take equity either.


Seed round sizes outgrew him.  Eric saw first hand how the size of seed rounds exploded.  Seed rounds went from $1mm to $5mm, and Eric wasn’t at the right place to take $5mm.  Rounds are larger, but investors want more traction.  Specifically, they wanted to see him do a few hundred thousand a month in bookings and he just wasn’t there.  Eric sees a hole in the market for founders looking for $150k to $500k checks.  Even angels were looking for seed traction, but wanted to write angel size checks.


So he bootstrapped.  As a result, Eric and his brother funded the company.  They maxed out all their credit cards and plowed their savings into the product.  There was no other option than to self fund but the stress was intense.  He recognized it could have screwed up Eric’s life if he had to go bankrupt and pay off debts for 20 years.


Growing users through influencers.  Eric and his brother did some PR but didn’t do much prior to launch because of limited funds.  They really focused on influencers and tastemakers. The company got a few thousand monthly uniques with no marketing dollars and 30% of traffic was repeat.  Organic traffic is the stickiest.  They soft launched to great metrics – people coming to the site were there for 5 minutes, the bounce rate was 27%, and, the click through rate to booking partners was 20% which is phenomenal. They started generating some bookings and had a ton of content. The company didn’t really try paid marketing yet.  They just didn’t have enough money to go with paid channels.


Problems with influencers.  Eric hoped the content creators would be the voice of the product and evangelize it.  That didn’t work out as thought: influencers with fewer followers didn’t have enough volume to impact the company.  Those with lots of followers wanted to be paid for participating.


Sell versus raise.  Eric determined an acqui-hire with a strategic travel brand made more sense than continuing to try and raise a seed round. Eric wanted the resources of a big acquirer and brand.  If an investor wanted to provide capital, it wouldn’t have been as interesting.    At the beginning of 2019, he reached out to 15 companies.  13 responded and 6 signed NDA’s. They had much more interest from strategic travel brands than lead investors.  Lonely Planet hired a new CEO at the time who was excited about TRILL and shared his vision.  They struck a deal and Eric became the VP of Ventures.  He’s now in charge of innovation for Lonely Planet.


Perfection is your enemy.  If Eric could do it all again, he would put the product out sooner.  Eric was attempting to achieve product perfection and in hindsight, that tweaking cost him valuable time.   Eric also would have reached out to corporate partners earlier on in the life of his business.


Big thanks to Eric for sharing his story.


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