Loving experiences ≠ Helping others have experiences

What is it like to

live through a pivot?

Google Cofounder Larry Page has a rule that Google only will acquire companies used as often as a toothbrush (e.g. every day, hopefully!) Adventurate was hobbled from the start in a way that many travel tech companies are. Travel for many people is infrequent, and adventure travel activities are something people do once every year or sometimes even two years. With my business model - a basic marketplace commission model - being dependent on repeat users and them spreading the word, I began to realize how treacherous the path ahead was.


I don’t even think venture capital would have made a difference: Zerve, a prominent company that had defined the website booking experience for the adventure travel industry, shut down in 2016. They had millions in investment and had been around for a decade. They had the benefit of a network and being first-movers. It didn’t help them to defy the toothbrush test that hinders adventure travel technology businesses.


Once I heard this business insight in year two of my entrepreneurial adventure, I realized just how precisely it summarized the problem Adventurate faced. I decided that the product decisions I made in the future would be scrutinized by this test.

Create products used as much as these...every day, hopefully!

Hello Friends,

Three years ago this month, I climbed the ladder into entrepreneurship and have been running my own app company ever since. Each year of my entrepreneurial journey has been transformative, but this year been the most epic yet. Through this blog, I hope to shed some light on what it is like to experience this adventure, and what it is like to successfully navigate a pivot.

About a year ago, I was faced with an existential business decision: continue working on the Adventurate adventure travel app, or pivot to something new based on my research and what I saw going on in the App Store. There were financial considerations: despite getting to the top 2% of travel apps, Adventurate wasn’t making enough money. The company wasn’t profitable, and I didn’t foresee the app helping it become so (even with an infusion of venture capital - more on that later). But there also was literally a countdown clock: Facebook was shutting down their backend server system that provided the infrastructure for tens of thousands of apps. On January 30th, 2017, Adventurate - and even the philanthropic SafeWater Flint app - would effectively be over unless I did a monumental overhaul to recreate the cloud backend, essentially starting from scratch.


On the other hand, I gained insights into apps that were telling me another direction might be better. As I was building business partnerships for Adventurate, I was making hundreds of calls. I developed an app to help speed up my call process, and began to see a potential that there’d be tons of others who would buy such a product. This app was, of course, the precursor to SwiftCall. As things looked bad for the travel app, I began to wonder about developing apps for businesses based on my personal insights.

As I faced the choice, I also had something else personally daunting: the travel app I worked on sounded like it was the “Next Big Thing”. Productivity apps? Yeah people may use those every day, but they don’t sound “cool.” To the layperson, it may have even sounded like I ran out of ideas. I had to be willing to forgo the “cool factor” to use the unique business insights that I had discovered. Business leadership, and pivoting, is sometimes about being bold enough to pursue something in a completely new, and well-researched, direction. I faced this choice at that critical moment.


I decided to do something different, and set out that day to follow what my experience had taught me. The result is a business that has expanded significantly, is now profitable, and has made it not only into the top 2%, but now the top 50 business apps.


​​The following principles helped me successfully pivot my company: 1) Follow the toothbrush test; 2) Limit funnels; and 3) Realize that loving experiences is different from helping others have experiences.

Follow the Toothbrush Test

Adventurate has paid apps only now. This means better sales and fair & transparent pricing.

What is it like to live through a pivot? In short, it is daunting. As I wrote in the original blog post, taking a leap into starting a business is a bold move. By the time someone is pivoting though, the thoughts are different. Once I started a company, continuing to be a business owner isn’t the daunting part. The scary part is admitting I was wrong.


Hindsight makes it easy and the past tense is comforting, but the pivot requires saying “I AM CURRENTLY wrong, but I want to make things right, and I am going to.” A pivot then is a monumental effort of self reflection. I am glad I was able to handle my company’s pivot with grace.

2018 is an exciting time for many reasons. Adventurate’s growth and future potential provides me with one more reason to be excited this year. Thank you to all of Adventurate’s users for helping my company find success in year 3 of this journey.


Best regards,

Jake Santangelo

​Founder & CEO of Adventurate, Inc.

What It's Like to Switch Careers and Run a Software Startup (Year Three)

I thought doing Adventurate would be just as fun as going on adventures. Not so, and not for obvious reasons. I enjoy app development, and thought creating an adventure app would be like creating a digital marketplace.


In reality, I began to realize travel tech actually entails being involved in the scheduling demands of a travel agency. I don’t enjoy that. It’s just like how enjoying craft beer is different from enjoyment of building a brewery. I wanted in the future to do something that would be rewarding from a business perspective and from a day-to-day perspective.


​There were many other lessons I picked up about apps in my time, but these were some critical ones that shaped Adventurate’s current product path.

Limit Funnels

I loved this kayaking experience in Miami. Scheduling it for others? Not as fun.

Funnels are the death of free apps. Free apps are dependent on users taking an action. Downloads can mean nearly nothing. I’ve heard horror stories of free apps with over a million users making $60 a month (and that’s not uncommon). It’s all about completion on an action, like making a booking or in-app purchase.


Adventurate’s funnel was necessarily extensive. It had to be, but in the future I wanted to go into apps that wouldn’t face such an issue. Partially because of this, I decided paid apps are the route I wanted to take. It’s not just something that has been beneficial from a business perspective: I genuinely believe paid apps are better for the user. An industry philosophy for describing free apps is to “steal the users’ time and sell it back to them.”


Not surprisingly, users don’t like being treated like lab rats, and people realize “free apps” are not really free. I wanted to eliminate the funnels that made earning revenue difficult, while also avoiding the funnel game that makes many apps so miserable.