The Ask Challenge
Lessons from an Anniversary Adventure
Last weekend, Jackie and I celebrated our 14th anniversary, and it was an absolute blast.
We stayed at the Hotel Magdalena, just off South Congress in downtown Austin. The hotel’s location was perfect, it was a short Uber ride from our dinner reservations at La Condesa, a MICHELIN-recommended restaurant a coworker had raved about. She also mentioned that it had plenty of gluten-free options, which made it ideal for Jackie.
Taking a Chance: The Equipment Room
Before dinner, I wanted to check out the speakeasy Equipment Room (or EQ Room for the cool kids) on the hotel's property. It’s a reservation-only spot that is fully booked online, but I figured it wouldn’t hurt to ask if there were any openings.
When the doors opened at 5 p.m., I headed to the hostess and explained that it was our anniversary. “Do you have any availability tonight?” I asked. Luck was on our side, they had an open spot at 8:30 p.m., which perfectly fit our schedule.
Exploring Austin’s Hidden Gems
Dinner at La Condesa was phenomenal. The flavors, the atmosphere, it all lived up to the hype. With some time to kill before our EQ Room reservation, we visited Small Victory, another hidden gem. This speakeasy, tucked inside a parking garage and marked only by a small “Bar” sign, didn’t disappoint. The drinks were creative, and we had some of the night's best conversations.
Afterward, we hopped in an Uber and returned to the hotel for our EQ Room reservation.
A Vinyl Experience Like No Other
The Equipment Room is more than just a bar, it’s a Hi-Fi Vinyl bar. A DJ picks vinyl albums from a massive shelf, creating a unique, immersive atmosphere.
As we settled in, the bartender surprised us. “You must know someone,” she said, pointing out that we were seated in a special spot. Then, they handed us two pairs of headphones. They let us hear the music in stunning detail, a feature we didn’t see anywhere else in the room. It felt like we had unlocked an entirely different experience, all because I’d taken the chance to ask. Jackie was even able to request a Beyoncé song even though it was not a request-a-song type of vibe.
The Power of Asking
This experience reminded me of something I teach my students every semester: The Ask Challenge.
I got the idea from Noah Kagan in the book Million Dollar Weekend to challenge them to go to a coffee shop and ask for a 10% discount, something small but uncomfortable enough to spark growth. Most feel embarrassed about being told no, but that’s the whole point. It’s low risk.
As an entrepreneur, you’ll constantly face situations where you need to ask:
Asking investors for funding.
Asking customers to buy your product or service.
Asking talented people to join your team.
Asking vendors for deals and partnerships
Rejection is inevitable, but so is growth if you practice asking. The fear of rejection holds many back, but it’s a skill set you can develop. Door-to-door salespeople face rejection every other minute but keep going. Why? Because each “no” gets them closer to a “yes.”
When I asked the students about their experience, most said it was awkward initially, but they all realized it was no big deal. Some also got their discounts, which was a plus.
Lessons from Asking
If I hadn’t asked about the Equipment Room reservations, despite the online system showing none were available, we would have missed out on one of the highlights of our night.
The same applies in life and business. The act of asking creates opportunities you didn’t know existed. It pushes you out of your comfort zone and forces you to confront the fear of hearing “no.”
So here’s my advice:
Don’t shy away from asking.
Embrace the possibility of rejection.
Use every “no” as a stepping stone toward a “yes.”
Because sometimes, the best experiences, the ones you’ll remember forever, start with a simple, bold question: “Is there any chance?”
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Don’t get captured,
