Still on a (Mile) High!

DSW Ambassador: Whitney Holtzman

I am in a state of withdrawal after returning home following a dream week in Denver. First, I must thank Emily Tucker and Conor Swanson, who spearheaded my incredible experience, answered every question along the way and showed an unwavering belief in a girl from Tampa.

Out of 400 applicants, I truly felt like the luckiest girl alive to be selected as one of 50 Ambassadors. For anyone wondering, the email letting me know I’d been selected came in while I was at the Taylor Swift concert, so it was truly a dream night.

View from Red Rocks Amphitheater

From the minute I accepted my invitation, the Denver Startup Week Ambassadors team rolled out the red carpet. Southwest Airlines amazingly provided a free round-trip ticket to and from Denver for ALL 50 Ambassadors. We got to choose our arrival and departure dates, and the ticket was booked for us. We also enjoyed two free nights at the AC Marriott right in downtown, as well as free Lyft rides to and from the airport and many meals throughout the trip.
I’d never been to Denver, so I arrived an evening early and ventured out to Red Rocks. As a kid from Florida, I was blown away by the spectacular views, mountainous terrain and vibrant color of the rocks themselves. The great thing about being out in the mountains is that everything is a built-in workout, so I got to see these spectacular views after a hike up to the top of Red Rocks.

For me, there were two main highlights throughout my Ambassador experience. The first was visiting the four companies (Evolve Vacation Rental Network, Guild Education, Gusto, and Ibotta) where we were given amazing presentations, swag and company overviews by the founders. As a startup founder and CEO myself, I was not only grateful for these leaders’ time, but also their honesty stemming from the journeys of building their companies. They treated us as equals and provided us with advice, inside looks and anecdotes that will serve us well in our own companies for years to come. We started out at Evolve, a vacation rental management company, close to becoming the largest of its sort in the country. Day 2 brought visits to Guild, which offers education as an employee benefit. They have partnerships with Chipotle, Disney, Walmart, and other massive companies. Guild, led by a baller female CEO, is truly breaking the cycle and changing lives in so many neighborhoods. We’d done a lot of walking around Denver, so it was great that by the time we got to payroll provider Gusto, we had to take off our shoes. We were delighted with a great fireside chat by their founders — one of whom slept on a mattress in a closet while they were building the company. And we truly felt at home, all cozy in our socks.

Day 2 Dinner at Polsinelli

The night of Day 2 brought an incredible dinner at the law firm Polsinelli. We dined with leaders from all around Denver on Polsinelli’s outdoor terrace, which overlooked the mountains and football stadium — can’t ask for a better combo than that for a Florida girl, who also happens to be a diehard sports fan. I’m still salivating from the farm-fresh, family style meal we were all served. The final day of our program concluded with a stop at Ibotta, which provides cash back for almost any purchase you could dream of. I mean who doesn’t want free money?! We had a panel discussion with their executives, followed by breakout sessions based on our interests. They also fed us delicious food and sent us home with tons of very cool swag. Our final lunch took place at Prologis. You may not have heard of them, but they do commercial real estate for companies like Amazon and Walmart. So yeah, they’re kind of a big deal.

I was truly blown away that every company founder was authentic, funny, down-to-earth, and incredibly smart. Not one of them wasted a word that didn’t have meaning during our conversations. Every company also had an incredible culture that felt like a family. I was amazed there were so many companies that felt like home just in Denver.

The second component of this life-changing experience that really stuck with me was the other Ambassadors I met. Everyone was kind, funny, humble down-to-earth and oh yeah, changing the world. From FinTech startups to Netflix, Carnival, Facebook employees, founders who connect VCs to women-owned companies, and life-changing startups that help women claim their maternity leave benefits, this was the most impressive group of individuals. Not only do I have 49 new amazing friends across the country, but I also formed amazing business contacts. My business, Social Victories, helps pro athletes build their brands, so I came away with amazing potential endorsement and partnership opportunities that would’ve taken me years to collect on my own.

I live by Maya Angelou’s saying that the only thing people remember is how you made them feel. I left Denver feeling incredibly loved and supported by the city and every person involved in the Ambassadors program.