What Could Possibly Go Right? A Founder’s Journey of Learning and Building

Being a second-time founder certainly comes with experience, and with the widespread expectation that I should know better by now.
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Two years into Palona, I am confronted every day by just how much I still have to learn.

That is precisely why Danny Meyer’s What Could Possibly Go Right? felt so personal. Though the title captures the familiar optimism that propels founders to start, the stories inside provide Meyer’s personal reckoning with everything that happens afterward.

My dear friend Shawn Walchef recommended the book after interviewing Danny on his Restaurant Influencers podcast, praising it as one of the best books he had ever read.

I was already a devoted reader of Setting the Table: The Transforming Power of Hospitality in Business, Danny’s landmark book sharing his philosophy of “Enlightened Hospitality,” which focalizes the customer experience and employee insights in a virtuous cycle of care.

Having worked at Microsoft, I understood customer centricity. Danny’s book, however, helped me see it through the deeply human lens of hospitality: how we make people feel, how we care and show up for our teams, and how those choices are the foundation of our culture.

What Could Possibly Go Right? is a story of his journey as a founder, and it hit much closer to home.

The book opens with Dany preparing to tell his team that he is closing Tabla, his Indian restaurant, after 12 years of operation. After years of taking pride in never having closed a restaurant, he shares that he found himself evaluating his success as a restaurateur: “Can I actually go through with this?” he writes, “Will this make me a failure?”

Those questions resonated with me. At the founder level, a business decision becomes inextricably linked with your self-perception when you have the weight of your customers’ and employees’ belief in your mission and capability on your shoulders. Not only can it feel as though you’re letting yourself down, but it can oftentimes feel as though you’re testing their trust.

My journey with Palona has given me plenty of reasons to reevaluate the expectations I put on myself.

When I entered the restaurant industry, I came with years of experience leading technology companies and teams to success, but I was entirely an outsider to this world. I did what I thought would help us grow. I went to conferences, met with operators, and invested in visibility.

I learned a lot from those efforts. I built relationships that I treasure to this day. But I will be the first to admit that I overestimated how quickly visibility would translate into winning business.

Recently, while discussing attending yet another event with my team, I had to acknowledge how much my view on the importance of brand recognition and awareness at this stage of our business had changed. We needed to make the decision - to allocate resources towards attendance, marketing assets, and employee time - with a clearer understanding of concrete outcomes that would come out of these investments.

That was certainly a palpably uncomfortable admission when I was the one that set the direction.

It meant that the intuition that I had from my experience, which shaped my assumptions, was wrong. And it meant that I had incorrectly used my tenure as a leader in technology as a heuristic to excuse myself from the rigorous analysis necessary to make a decision that used time, money, and the team’s energy – which are real commitments.

In his podcast with Shawn, Danny said: “Sometimes you have to loosen your grip and let other people hold the racquet.”

I think about that alongside something like “founder’s intuition”. There are moments when your gut recognizes a mismatch before you can articulate it. That instinct deserves attention. So do the people around you who see something you have missed.

I am learning the delicate balance of holding my convictions firmly enough to act, but openly enough to let my team feel comfortable challenging me, because they know that they could change my mind.

There are, of course, also moments when things go incredibly right.

One of mine happened at Shawn’s own restaurant, Cali BBQ.

On Father’s Day, the team is so busy serving guests that it normally cannot accept phone orders. In 2026, Shawn AI, the Palona agent we built with him, captured 22 additional orders worth $1,905. Those were orders the restaurant otherwise would not have been able to take.

What stays with me is the trust behind that result. Shawn let something we built become part of how his restaurant welcomed and served people on one of its busiest days.

For a founder, there is something profoundly rewarding about seeing your idea become useful in someone else’s life, and to be a part of a moment where they feel the promise of your idea. The restaurant could serve more customers while its people stayed focused on the guests in front of them.

Danny asked Shawn another question that brings this back to its purpose: “Can we create businesses that genuinely make people’s lives better?”

That is what I want Palona to do.

Reading this book, I appreciated Danny’s willingness to look closely at his disappointments while remaining open to possibility. His honesty gave me room to reflect on my own mistakes without letting them define the whole journey.

I can wish I had made some decisions differently and still be deeply grateful that I started.

There is plenty I would revise in our original plan. But the belief that brought me here remains: we can build technology that helps people run better businesses and take better care of their customers.

So, though I am still asking what could possibly go right, I am certainly more willing to talk about what has gone wrong along the way.

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