Risky Business? These Women Say It’s the Smartest Move You Can Make

What does it really mean to take a risk in hospitality—and why are women so good at doing it differently?

That’s what we explored in our latest hertelier LinkedIn Live with two powerhouse guests: Dina Belon, President of Staypineapple, and Davonne Reaves, Founder of Vesterr and The Vonne Group.

Both women have built bold, game-changing careers—without waiting for permission. From leading tech overhauls to launching new businesses (and yes, weathering failures too), their stories offer practical wisdom for any woman ready to take the leap.

Clockwise: Davonne Reaves, Dina Belon, Emily Goldfischer and Nancy Mendelson

Here are 7 top takeaways from our conversation:

1. Redefine Risk: It’s Not Reckless—It’s Intentional

Risk isn’t always about leaping without a parachute. For Dina, it’s stepping into the unknown with purpose. “You won’t always have all the information,” she said. “You have to use gut and intuition—and take the leap anyway.”

Davonne’s early moves were risky, but grounded in purpose: an unpaid internship after college, moving to Boston without knowing a soul, and starting a company during uncertain times. Her philosophy? “If I think about it too much, I’ll get scared. So I just do it—and figure it out as I go.”

2. Tell People After You Jump

One of the most crowd-pleasing moments? Both Dina and Davonne said they often don’t tell people about a big decision until after they’ve made it. Why? Because even people who love you can fill your head with doubt.

“If you can’t help me cross the finish line,” Davonne said, “there’s no point in telling you. I don’t need your fears clouding my vision.”

3. Failure Isn’t Fatal. It’s Feedback.

Davonne’s first deal with Vesterr fell through. Investors had to be refunded. Confidence took a hit. “It was brutal,” she admitted. But her response? Lean into the lesson, not the shame.

That failure became her turning point. She revamped systems, tightened operations, and built a stronger team. Today, Vesterr has funded four deals and created over 100 Black hotel investors—most of them women.

Dina had her own detour into sustainability consulting that didn’t pan out long-term. Her lesson? Fail faster. “Don’t stay stuck in a role or culture that doesn’t fit. You can explain a short stint. It’s worse to waste years not growing.”

4. Women Think Riskier—But We Need to Act Riskier

From job applications to major life choices, women often wait until they feel “100% ready.” Dina pointed out that men will go for opportunities with 60% of the qualifications—women often won’t apply unless they have 90%. “We need to stop disqualifying ourselves.”

Davonne agreed, adding that risk aversion is not just gendered—it’s generational. “I grew up being told to follow the rules. But once I started creating my own path, everything changed.”

5. Change Agents Aren’t Just Visionaries—They’re Problem Solvers

What makes a change agent? Both guests agreed: it’s the mindset of seeing problems and wanting to fix them.

Dina brings her background in project management to leadership, constantly looking for better, more efficient ways to do things. “The culture at Staypineapple is always evolving,” she said. “We don’t over-document. That creates inertia.”

Davonne put it simply: “Either you complain or you change. But you can’t do both.” It was her frustration with lack of access to capital for women and people of color that led her to create Vesterr.

6. Know Your Non-Negotiables

Every strong leader has their compass, and for Dina, it comes down to three non-negotiables: trust, clarity, and accountability.

• Trust, she explained, is the foundation of everything—from team dynamics to guest experience.

• Clarity means being explicit about your vision so people know where you’re headed.

• Accountability? That’s the follow-through. “If you say something’s important and then don’t hold people to it, trust falls apart.”
  

She shared a metaphor that stuck with the group:“Trust is the boat. Inspiration is the wind. And when the wind dies, you need the boat to stay afloat.”In other words, inspiration might come and go—but when things get hard, your values and consistency are what carry you through.

7. Authenticity Is a Leadership Superpower

Davonne’s advice to her younger self? Ask more questions—and stop shrinking.“I used to think asking questions made me look dumb. Now I know it shows curiosity and confidence.”

She also made a strong case for owning your personal brand: “People know I love Beyoncé. I wear sneakers to conferences. I love green. That’s me. And if you don’t like it... that’s your problem.”

Authenticity builds trust, and trust builds influence. It’s that simple.

Final Word? Own Your Ambition

Whether you're running a company, launching a business, or just trying to step into something new, the message from Dina and Davonne is clear:

• Go for it!

• Don’t wait to be asked.

• If it doesn't go to plan, learn and move on.

• When it does work, will be so happy you tried!

  
  

Special thanks to our sponsor Staypineapple, the bold, playful, people-first hotel brand making waves in hospitality and supporting important conversations.

These are just the highlights, you can watch the full video here.

What risk are you ready to take? Tell us in the comments or share and tag us on LinkedIn!