Five Lessons from Five Years of Wheels Up Collective

I’m so excited to be in a position to write this month’s newsletter intro. Five years ago this month, Elise Oras and I started Wheels Up Collective.

We were knee deep in the COVID lockdown—remember when we all thought it was only going to be “two weeks to flatten the curve?!” ChatGPT wasn’t a thing, people were hoarding toilet paper, Black Lives Matter was drawing global attention, X was still Twitter, and you could buy a bitcoin token for under $6k. Zoom was not a household name, and remote work was largely reserved for startup tech life. Five years ago seems like a lifetime. And while everyone else was making sourdough starter, we started Wheels Up. 

Elise and I were both at arguably the height of our careers and were coming off jobs that weren’t great culture fits. We were both frustrated, tired, and just sad about work. Both of us were ambitious about growing professionally and doing great work, and we were hungry for an environment that gave us the support, resources, and encouragement we needed to grow. 

But, we were also very much at points in our lives where there was more to life than just work. Call it a mid(?) life crisis, but I had been on a plane 50% of the time, and it was exhausting. If you know me at all, you know I’ve been an avid equestrian my entire life. It’s a creative outlet, a meditation, and a physical and mental challenge. I’m a better marketer (and person) when I am able to get out to the barn and hang out with a horse regularly. Sadly, few ambitious careers can be the yin to this yang. And the not surprising thing is that there are so many (women especially) who have similar dichotomous lives—parents, spouses, world travelers, committed amateur athletes, crafters, gardeners, or whatever—it doesn’t fit into the “regular” 8-6 desk job professional life. This part of the workforce is largely ignored and passed over due to a lack of work-life flexibility. And what a shame. These are the most ambitious, motivated, and creative people. 

So that was our North Star. Elise and I set out to build a place where our team members could each do the best work of their careers, on their terms, and according to their schedules. They could live vibrant lives outside of work, then log on ready to hustle. And we’ve held true to that. We have a robust tech backbone paired with some kick ass project managers that, together, enable mostly asynchronous work for the whole team. 

The biggest piece of the puzzle, though, is that we hired the absolute best rock stars we have ever worked with. We curated a team of our favorite people. The coworkers you love working with because you make each other better and faster. And usually these rock stars are not only good at their jobs, but also just good people, bringing transparency, accountability, honesty, and trustworthiness to the table every day.

Along the way, we’ve learned a lot. Some lessons were hard-earned, others were gifts, and a few were just common sense confirmed by time spent in the trenches. Here are five things I now know for sure after five years of growing this business.

1. People. Are. Everything.

I shared a little about the importance of finding the best teammates. But it extends to clients and partners as well. Who you choose to work with is the single biggest factor of your success. Hire people you trust. Work with clients who can grow to trust you. Collaborate with partners who understand your quirks and turn them into strengths. Working with the wrong people—on any front—will drain your time, energy, and sanity. Choose wisely, even if it means keeping a req open longer than you’d like to, or turning down a client when you really could use the work. 

Case in point: If you’ve worked with us at all, you know Diana Sparacio. She was never supposed to be a Wheels Up team member. Right out of college, Wheels Up was just a few hours on the side while she relocated to Seattle and looked for a local job. Well, Diana never made it to Seattle, she never got that other job, and she is now our Head of Operations. We absolutely could not operate today without her. And I wouldn’t want to. She comes to work every day with a smile and a laugh and keeps us all on task and we absolutely love her.

2. The Universe Has a Funny Way of Working Things Out

As a card-carrying Type A’er to the grave, this one has been so, so (SO) hard for me to embrace. If you stay focused, and hustle, and set a course tearing towards your intentions, you’ll usually get there. It may not be the way you planned, but things have a funny way of working out if you have a little faith and patience. 

The biggest test of this for me was in 2022. The tech recession hit us really hard. We lost a lot of business, as did our clients. But it was also the year we had four Wheels Up babies born and three team members who wanted to take extended leave. We load-balanced schedules and work queues, made strategic shifts, and kept every single person on the team busy enough that no one had to find another job. 

It’s so hard to trust your path. That year was probably the hardest time in my professional life; I never anticipated the stress associated with running a company that provides a livelihood for others. But our team pulled through and the business bounced back. (And let me tell you, those are the cutest kids in the world.) 

There are many examples like this that we’ve had through the years. We try to stay focused on our convictions, and make the best decisions we can. We play the long game. In 2022 I learned the valuable lesson that success doesn’t always mean growth—it can mean survival, too.

3. It’s OK to Have the Hard Conversation

When you’re on our side of the client/agency relationship, it’s really easy to convince yourself that you’re constantly on the verge of getting canned. Or at least it is for me. Call it PTSD from a professional lifetime on the startup rodeo rollercoaster, but I very frequently assume the worst.

This can cause an unintentional chilling effect to client/agency communication. In that mindset, it’s easy to back off a bold recommendation or soften news that’s going to spark a tough conversation.

It’s universal in high stakes, fast paced situations: It almost never pays to pull back. We frequently remind ourselves that our clients hire us to give them advice. It’s up to them if they take the advice, but it’s on us to give them the best advice we can, even when it’s going to be unpopular. 

Very early on, Elise and I were onsite with a client for a strategy planning session. The team had identified a few roadblocks, and after spending a lot of the day unable to come up with actionable resolutions, I perhaps became a little, um, animated. I vividly remember being mortified when after the meeting was over, Elise called me from the airport: “OK. So, new rule. No yelling at clients.” (Insert cringe emoji.) I smoothed over everything and they are still one of our most favorite accounts, so all’s well that ends well. But more importantly, they trust us to tell them the truth. Not because of what happened that day, but because for years, we’ve always been upfront, candid, and honest about the work, the strategy, and the relationship. I’m incredibly grateful that the CMO didn’t fire us that day. And I’m also incredibly grateful that he and his team have been authentic colleagues and true partners and that we’ve been able to do some remarkable work together.

4. Know Who You Are—And Stick to It

Five years ago, I sat down with Elise and our good friend and Wheels Up designer Andrea Moon to try to define who we wanted to be. On the back of a napkin, we came up with our core values: hustle, reason, empathy, and wit. We workshopped them with the whole team and all felt pretty good about where we landed. I knew from working at Socrata that well-defined core values can be the guardrails that very literally keep a company on track. But Andrea pushed us to define guiding tenets, too: the way we behave, the things that are important to us. Be kind. Live with balance. Be authentic. Make it count. Strive for Better. Reliably deliver. 

Our poor website is so outdated, but when I look at the Team page, I still love every single word of it. I am so proud of the culture we’ve created. And I’m fiercely protective of it.

We’ve turned down working with teams that aren’t a good match and we’ve said no to work that wasn’t in our wheelhouse. Again, it’s so hard to walk away from business, but in retrospect, it’s always been the right decision. Sometimes saying no is just as important as saying yes. We’re not for everyone. But if we’re your kind of people, then we’ll be the best you’ll ever work with. 

5. It’s OK to Have Imposter Syndrome, But It’s Also OK to Dream Big 

There are days when the imposter syndrome is crippling. (Am I alone here??) This is why you need to get yourself a partner like Elise. She buoys me right back up with the best “get your sh!t together, you’re being ridiculous” pep talks. These moments of insecurity rarely have anything to do with the actual marketing work that we’re doing—that’s the easy stuff. When it hits, I try to tether myself to my own North Star. 

Kevin Merritt, the CEO at Socrata, made a comment early in my days there that he wanted to make that company a place where every employee could do the best work of their career. I always loved that. But my take on that is this: Yes! And, I want Wheels Up to be the last place every one on the team works because it’s such a great environment, it’s so inspiring and fulfilling and rewarding, and it’s sufficiently lucrative that we can live full lives and be our best selves. Ultimately, it’s such a great place to work, there’s no reason to ever leave. That our clients’ businesses are more successful because of us, and in turn, their lives are enriched. 

So that’s my North Star and my big dream. Do the right thing for the people around you. Help where you can, give what you have, and that along with a little faith that the universe will take care of you, and things will work out for us. 

Wheels Up? You Bet.

I named this company for my Dad, who was an avid hobby pilot and always said “wheels up” when talking about what time something was happening. I thought it fit with what we’re trying to do—to help companies going through a rapid transformation get their own proverbial wheels up. I don’t know that Elise and I had a vision of what things would look like in 5 years when we started it. Honestly, I mostly thought of it would as a COVID project. But 5 years later, I can’t imagine doing anything else. There are days when it consumes every piece of my soul, and there are days when I am overcome with pride for the team. I have had the chance to work with super smart clients who I now consider genuine friends. We’ve had Wheels Up babies for goodness sake!! (5 on our team, plus twins due in November!!) We’ve been along for the ride for weddings and funerals and mortgages and funding rounds. I’d guess that there have been Wheels Up Zoom calls in almost every state in the country by now! 

We’ve come a long way, but we’re just getting started. I’m overwhelmed with gratitude for our team, our clients, our cheerleaders, and friends. Here’s to what’s next! I hope you’ll join us for the next 5 years.