Startup Success On a Scale of 0 to 100 - How likely are you to succeed?


The idea

It was barely two years ago when I asked my wife to sit down because I had something “kinda big” to tell her. Her face turned a whiter shade of pale as she sunk slowly into the couch. Having been married to me for almost two decades she’s accustomed to my “big ideas” but when I ask her to sit down she knows that her life — our life — is about to change.

As I began to describe the concept for the — then unnamed — RISE (ask me sometime about the terrible, horrible, no-good, very bad original name), she lovingly listened, nodding with acceptance and genuine intrigue…but no doubt picturing the chaotic months (years) sure to follow.

Angela and I had been through a handful of these “I think this idea has the ability to be big,” moments. Most, although not all, of those were worth the pain and angst that a startup brings to a relationship (although, to be frank, I typically downplay the failures as “casual ideas” and the successful ideas as the “big ideas” even though they all started with relatively the same level of enthusiasm and optimism).

The first employees of RISE spent the next 12 months getting the technology built, marketing tuned in, investors lined up, operators vetted, sales and operations processes established and — most importantly (and painfully) — government certificates awarded (we are the first company to launch this type of service in partnership with operators using OPP… “Other People’s Planes”).

Although we have lost countless hours obsessing over every detail of this complex and unpredictable business, we now sit here, with a viable and growing business that is changing the way the world purchases, accesses and experiences air travel. As I dissect it by the numbers and marvel at what we have accomplished in such a short period of time, I found that the numbers didn’t just point to milestones for RISE but they created a “startup scale” of sorts that highlighted some important lessons for me and anyone making that breathless and frightening leap into unchartered territory.

Some of the amazing RISE Employees who work tirelessly to serve our members

Some of the amazing RISE Employees who work tirelessly to serve our members

The Scale


Zero is the amount of aviation experience I came into this business with. RISE was born from a desire to fix what was a very broken process by providing a viable alternative to commercial air travel. Our mission was simple…give people back the most valuable commodity in the world — time.

Zero is also the amount of plane debt we have in RISE. By utilizing underutilized assets in the business aviation sector we fulfill our mission and lean on highly qualified operators to fullfill the operations of RISE.

Lesson: Don’t let what you don’t know stop you because they will sometimes lead you to the most creative and unconventional solutions.


10 months into operation, RISE is flying its 10,000th member while providing a 10x better experience over flying commercial at 10x less the cost of flying private.

Lesson: If you build it with purpose and a laser focus on creating something truly great, they will come.


As in the 20 seconds or less it takes our members to book or cancel a flight on RISE using our proprietary technology stack (with no change fees, cancelation fees or baggage fees).

Lesson: Technology must be at the forefront of what you create. All the marketing slogans and media hits in the world can’t make up for a subpar technology experience.


Approximately 30,000 hours have been given back to our members by eliminating all the lines and hassles associated with commercial travel.

Lesson: Don’t just stay true to your mission…make it measurable.


The number of employees on the RISE payroll. Very few people realize this but RISE exists to take care of its employees. We have stated this from day one as we feel that it is one of life’s highest honors to provide a stable, safe and well-paying work environment for an employee. Beyond that, we feel an obligation to help understand our employees and what they were created to do so that we can do our part to enable their calling in this world. RISE is heavily weighted with Millienials as employees and we love them (see my previous post: Millenials, I was wrong about you. Please forgive me). We don’t just see it as our job to provide a paycheck to our people but to groom them, guide them and teach (as well as learn from) them.

Lesson: The single most important thing in any business is people. Surround yourself with those that have the hunger, drive and desire to see your mission through.


Our operators are seeing more than a 50-percent increase in utilization due to RISE. As a result, they are adding more jobs, providing pilots more hours and purchasing more fuel which, in turn, lifts the communities we serve.

Lesson: Businesses that value all the stakeholders are the best businesses of all.


Number of weekly scheduled RISE flights between the cities we serve. As we start to expand our services and offerings, we must remember that our core product — providing reliable, scheduled service between key business cities — built the foundation of this business and will always be a key part of our future success no matter what areas we expand into.

Lesson: Don’t lose sight of your core even as you start to rapidly expand.


More than 70-percent of our members have never flown on a private plane before joining RISE which proves we aren’t just re-defining how the ultra-wealthy travel…we’re carving out a completely new category. The sharing economy is real at every level of the economic scale.

Lesson: Just because it hasn’t been done before doesn’t mean it can’t be done….it just means you are defining it.


The percent of RISE employees that are member-facing each and every day. In short, they are our brand.

Lesson: Keep the main thing the main thing as you grow.


As in our +97 NPS score. This metric fuels our business. The fact that it’s so high is actually pretty terrifying because there’s very little room to move up and a very long way to fall.

Lesson: Find that one metric that keeps you focused and never lose sight of it.


The 100% confidence I have that this business will continue to thrive as long as we stay true to our vision and purpose.

Lesson: Staying confident is, by far, the hardest part of this journey. When you falter, remember that you are out to accomplish something bigger than yourself. Find your purpose and the rest will take care of itself.


The first step is the hardest

Starting a company is one of the scariest things you will ever do. Most visionaries don’t know the exact details of how they will find success, but we do know that come hell or high water we can get to the end goal.

The best visionaries know three things intimately:

  1. Where they currently stand; this is necessary to understand how long the journey will be. Although it is always longer and tougher than they can ever imagine (see Why every founder should do an Ironman)

  2. Where they want to go; the end goal is crystal clear and they will not waiver from it.

  3. What their biggest weakness are; so that they can surround themselves with people who are smarter and better than they are in those areas. This is often the hardest part because admitting you don’t have all the answers is humbling and seemingly against the visionary ethos.

Any truthful entrepreneur will tell you that they are making it up as they go and yet everyone from your investors, to the media, to your employees want to know that you know what the hell you are doing. (Hint: If what you are doing has never been done before, they know you don’t know and its okay to admit it so they can help you.)

At RISE we recently took personality tests and the results were given to all of our employees. Tracy Timm has helped us implement the Predictive Index test within RISE and the results were amazingly accurate and has helped us tremendously in finding the right fit for our employees. When I received my results I asked the Tracy to ELI5 (Explain it to me like I am five years old) and she told me “you often open your mouth and start a sentence without knowing how it’s going to end.” I think she wanted me to take that as a learning experience for me, and I did; my team knows how much I am working on this to make their lives easier. But I also chuckled to myself realizing that’s exactly what visionaries do, we start things not knowing how it’s going end but believing enough in our teams that we will find a way to success.

That is exactly what I did two years ago with my wife, I started a journey knowing where I wanted to go but not knowing how to get there. The 40 amazing RISE employees and the numerous other people have helped make RISE a reality; I started the sentence and they are now in the process of completing it.

Now that we have flown 10,000 members I can’t wait to see the journey as we reach the milestone of 100,000 members flown. Even at that point we will only be barely getting out of the starting gates of where I originally envisioned RISE to be when my wife graciously encouraged me on this journey.

Travel Better,


RISE was the next generation of air travel where lines no longer exist, time is no longer wasted and travelers are not merely passengers but members of a like-minded community of successful professionals. This is travel the way it was intended to be.