Richard

When people ask how I ended up building a real estate technology company after studying architecture, I usually smile, because the path makes more sense than it sounds.

Architecture and entrepreneurship may seem like different worlds. One deals with buildings, materials, structure and space. The other deals with products, customers, systems and growth. But after years of moving between architecture, real estate and technology, I’ve realized they’re deeply connected. Both are about solving problems for people.

A building isn’t successful just because it looks beautiful in a rendering. It has to work. People have to move through it naturally, and it has to respond to light, function, structure, budget and daily life. The same is true for a business. A company can have a beautiful logo, a polished website and a slick pitch deck, but if it doesn’t solve a real problem for real people, it will eventually crack.

Here are a few lessons architecture taught me about building a better business.

Start with the people who will use it

In architecture school, we were trained to think about the user before falling in love with the design. Who is going to live here? How will they move through the space? Where will they sit in the morning? What will annoy them after six months? That way of thinking stayed with me.

When I first entered the real estate industry in New York, I noticed something that seemed obvious but was strangely ignored: Apartment hunters were frustrated. Listings were confusing, photos were overly polished, and sometimes the apartment looked nothing like the ad. Anyone who has apartment-hunted in New York knows the feeling. You show up excited, open the door and immediately think, “Wait, this is not what I saw online.”

That frustration became the foundation for my company. The idea was simple: Show people real, unedited video tours so they can understand a space before wasting time visiting it.

My advice to entrepreneurs is to resist the urge to start with what you want to build. Start with what people are struggling with. Listen closely, and watch where they get confused, annoyed or disappointed. The best business ideas often don’t come from trying to impress people. They come from removing a specific frustration from their lives.

Function comes before beauty

I studied architecture, so of course I care about aesthetics. But architecture taught me that beauty without function is fragile.

A stunning house with awkward circulation is still awkward. A beautiful lobby with poor lighting still makes people uncomfortable. A perfectly designed room that doesn’t fit the way people actually live is more sculpture than home. Businesses fall into this trap all the time.

I’ve seen founders spend months perfecting their branding before confirming that anyone wants the product. I’ve seen websites that look incredible but make it nearly impossible to book a call. I’ve seen companies describe what they do in language so polished and abstract that no one understands what they’re selling.

If this sounds familiar, I’ve been there too. In the early days of building my company, I sometimes wanted things to look more sophisticated than they needed to. Over time, I learned that clarity is more valuable than complexity. People don’t need your business to sound impressive. They need to understand how it helps them.

If you’re building something, ask yourself: Does this work before it looks perfect? Can someone understand the value quickly? Can they take the next step without a manual, a follow-up email and three “emotional support” coffees?

Beauty matters, but function earns trust.

Constraints can make you more creative

One of the first things architecture teaches you is that constraints are everywhere: budget, site conditions, structural limits, zoning rules, materials, deadlines and client preferences. Reality, basically.

At first, constraints feel annoying because they interrupt the fantasy. You have an idea, and the world gently says, “Cute, but no.” Eventually, though, you realize constraints aren’t always the enemy. Sometimes they’re exactly what forces you to design something better. Entrepreneurship works the same way.

When you don’t have unlimited funding, you get sharper. When your team is small, you learn to prioritize. When you can’t build every feature, you focus on the one that matters most. Some of my best business decisions came from not having enough resources to do everything.

I’ve seen this lesson play out again and again in my family’s urban development work in Mexico. Growth doesn’t happen all at once. You work in phases: You improve access, add infrastructure, subdivide land and wait as the city expands. It isn’t glamorous, overnight success, but it works because it respects sequence, timing and reality.

For entrepreneurs, constraints can be a gift if you stop fighting them long enough to learn from them. The next time you feel limited, don’t immediately ask, “How do I get more?” Ask, “What is this limitation forcing me to clarify?” You may find you don’t need more money, people or time. You may just need a better order of operations.

Design the experience, not just the product

A building isn’t experienced all at once. You approach it, enter it, move through it, discover it, use it and remember it. That sequence matters.

The same is true for business. Customers don’t just experience your product. They experience your emails, website, response time, onboarding, explanations, invoices, mistakes and follow-ups. Everything counts.

In real estate, I learned quickly that clients weren’t stressed only because they had to choose an apartment. They were stressed because the process felt unclear. What happens after the application? What documents are needed? How fast do they need to move? What should they watch out for?

Once I started explaining the process before people had to ask, the entire experience changed. The service became easier, clients became calmer and trust grew faster. It taught me one of my favorite business lessons: Confusion is expensive. It costs time, energy and trust, and sometimes it costs the sale.

Here’s the exercise I recommend: Walk through your business as a customer who knows nothing. Where would you hesitate? Where would you feel unsure? Where would you need reassurance? Then redesign those moments.

Add a checklist. Simplify the email. Create a short video. Rewrite the confusing paragraph. Remove one unnecessary step. A great customer experience is rarely about adding more. More often, it’s about making the path easier to follow.

Build something that can evolve

Buildings change. Families grow. Neighborhoods shift. A space that works today may need to become something else later. Good architecture allows for change, and good businesses should too.

The world moves too quickly for rigid companies. Customer expectations shift, technology evolves, markets surprise us and competitors appear out of nowhere. Sometimes, what you thought your business would become isn’t what the market actually needs.

When the real estate industry went digital, especially during and after the pandemic, companies had to adapt quickly. Virtual tours, remote communication, digital paperwork and faster follow-up went from luxuries to expectations. Businesses with room to evolve adjusted faster.

That’s why I believe entrepreneurs should build around the problem they solve, not just the product they currently offer.

I started my company with a simple belief: Real estate should be more transparent. Unedited video tours were one expression of that belief, but the mission is bigger than the format. As technology evolves, the tools may change. The principle stays the same.

If you’re building a business, stay loyal to the problem, not to the first version of your solution. Your first product may not be your final product. Your first customer may not be your best customer. Your first business model may not be the one that lasts. Leave room to grow.

Architecture taught me that the best designs aren’t the loudest. They’re the ones that work so well people barely notice the effort behind them. Business is the same. The best companies make life easier. They reduce confusion, respect people’s time, solve real problems and are built with intention.

Looking back, I don’t think I ever really left architecture. I just changed materials. Instead of designing buildings, I now design systems, experiences and businesses, and the lessons remain the same: Start with people, respect the constraints, make the path clear and build something that can stand the test of time.

Because whether you’re creating a home, a company or a life, good design is never just about how something looks. It’s about how it works.

When people ask how I ended up building a real estate technology company after studying architecture, I usually smile, because the path makes more sense than it sounds.

Architecture and entrepreneurship may seem like different worlds. One deals with buildings, materials, structure and space. The other deals with products, customers, systems and growth. But after years of moving between architecture, real estate and technology, I’ve realized they’re deeply connected. Both are about solving problems for people.

A building isn’t successful just because it looks beautiful in a rendering. It has to work. People have to move through it naturally, and it has to respond to light, function, structure, budget and daily life. The same is true for a business. A company can have a beautiful logo, a polished website and a slick pitch deck, but if it doesn’t solve a real problem for real people, it will eventually crack.

As a six-time CEO who has served on 23 corporate boards, I’ve watched the same story unfold in nearly every sector. An ambitious founder builds a business, reaches the point where they want to step back from daily operations, hires a CEO and moves into the chairman role, assuming the hardest work is behind them. Six months later, the relationship starts to fracture.

The founder feels the new leader is moving too slowly or making different choices, while the CEO feels micromanaged and stripped of authority. Once that trust breaks, the transition meant to unlock the company’s next chapter becomes a source of friction and lost momentum.

Having navigated this handoff from both sides of the table, I call this dynamic “the chairman’s gap”: the gray zone between providing governance and interfering. Staying on the right side of that line doesn’t happen by accident. It requires unlearning the operational habits that made you successful in the first place.

Unlearn the operator mindset

When founders ask me how to make the move from founder to chairman, they usually expect a tactical playbook on board meetings or governance structures. The mechanics matter, but I’ve found the real challenge is psychological.

As an operating CEO, your daily survival depends on answering “how.” You inspect details, solve bottlenecks and drive execution. As chairman, you have to give up ownership of the “how” and focus on the “what” and “why”: setting strategic direction, securing capital and holding your CEO accountable for results.

I put this into practice when I co-founded a luxury vehicle business. I knew from day one that I wouldn’t run daily operations, so I brought in an industry expert I had mentored for five years as president and CEO. Even with decades of executive experience, I still had to train myself to stay in my lane.

If you’re wondering whether to hire a CEO, the real question is whether you’re prepared to let someone else run the business differently than you would. If our CEO evaluates an opportunity differently than I would, my job isn’t to override that decision. It’s to support the culture of accountability we built together. Different isn’t wrong; it’s just different. When a chairman accepts that there are multiple routes to a goal, the partnership thrives.

Define what a chairman actually does

Adopting that mindset is essential, but making it work day to day requires clear structure. Most executive friction comes down to a simple oversight: Neither leader defined where their authority starts and stops on day one. Working well with the CEO you hired means setting explicit rules of engagement long before you hand over control.

Across my board experience, a chairman’s role falls into three areas:

• Capital and governance: securing financial backing, protecting resources and maintaining fiscal oversight through formal board channels.
• Advice and mentorship: serving as a trusted sounding board when the CEO wants perspective on high-stakes decisions.
• Foundational support: stepping in temporarily on administrative areas where the CEO needs help, such as reviewing insurance policies, setting up banking or building back-office systems.

Notice what’s missing: managing inventory, dictating daily workflows or going around the CEO to direct staff. With our CEO, I stay informed through a simple routine: a formal monthly financial review, dual authorization on major transactions and quick high-level updates. That gives me clarity without putting my hands back on the wheel.

Know the line between oversight and interference

Knowing the difference between constructive oversight and interference is a critical skill for any chairman. From the outside, asking questions in a meeting or reviewing performance metrics can look the same either way. From the inside, they reflect opposite approaches to leadership.

Oversight focuses on outcomes and alignment: Is the team hitting its targets, protecting its values and managing risk? Interference focuses on personal preference: Why was that email phrased that way? Why wasn’t the meeting run the way I used to run it?

When chairmen interfere, it usually comes from an emotional attachment to old routines. Early in my board career, whenever I spotted an inefficient process, my instinct was to jump in and fix it.

I quickly realized that doing so undermines the CEO’s confidence and destroys accountability. When you spot an issue as chairman, your job is to raise it with the CEO in an advisory conversation and leave the execution entirely in their hands.

Answer this question first

Mastering this discipline is what unlocks the real value of the chairman role. Giving your CEO room to execute frees you to focus on strategy and scale your impact without burning out on 80-hour workweeks.

But that success depends on one non-negotiable boundary. Before you sign a contract, post the job or even think about handing over control, ask yourself: Am I truly ready to let go, and will I trust the new CEO?

If the answer is yes, hand over the keys completely. Trust the leader you chose, hold them accountable for outcomes and give them room to drive. But if you hesitate, even for a moment, don’t hire a CEO. The biggest threat to a company’s next chapter isn’t a new executive making an operational mistake. It’s a chairman who refuses to get out of the driver’s seat.

As a six-time CEO who has served on 23 corporate boards, I’ve watched the same story unfold in nearly every sector. An ambitious founder builds a business, reaches the point where they want to step back from daily operations, hires a CEO and moves into the chairman role, assuming the hardest work is behind them. Six months later, the relationship starts to fracture.

The founder feels the new leader is moving too slowly or making different choices, while the CEO feels micromanaged and stripped of authority. Once that trust breaks, the transition meant to unlock the company’s next chapter becomes a source of friction and lost momentum.

Having navigated this handoff from both sides of the table, I call this dynamic “the chairman’s gap”: the gray zone between providing governance and interfering. Staying on the right side of that line doesn’t happen by accident. It requires unlearning the operational habits that made you successful in the first place.

Nuveen just closed its $13.1 billion acquisition of Schroders, the 222-year-old British asset manager. The deal pushes Nuveen into the top 10 global asset managers, with $2.6 trillion under management.

The headline is the money. The more interesting part is what CEO Bill Huffman said about culture. After more than 10 acquisitions, he has a clear view of how most mergers go wrong. The acquirer walks in, decides it knows better, and starts making everything its way. His alternative is simple. The first job after a deal is listening and learning, “Right? Not telling.”

He’s right. And it won’t be enough.

Not because Huffman doesn’t mean it. Because a cultural declaration, no matter how sincere, doesn’t tell anyone what to do differently when they walk into the next meeting.

Declaring is not leading

Leaders love to declare culture. “We’re customer obsessed.” “We’re one team.” “We listen before we act.” Each statement is true in the leader’s head. In everyone else’s head, it’s an abstraction waiting for a definition.

And people will supply that definition themselves. A Nuveen operations lead hears “listen and learn” and thinks it means delaying system integration. A Schroders portfolio manager hears it and assumes nothing will change. A finance director hears it and decides it’s a nice line from the CEO that doesn’t apply to budget consolidation. Three people. Three cultures. One declaration.

This is the Translation Gap. Strategy is set at the top. Execution happens at the front line. The layer in between, where an idea gets converted into what people actually think and do, gets left to chance. Leaders assume the concept is self-explanatory. It never is.

When the gap goes unaddressed, people default to what they already know. And in an acquisition, what the acquiring company already knows is how to be the acquirer. That’s exactly the behavior Huffman is trying to prevent.

Culture lives in mindsets and behaviors

Culture isn’t what leaders say. It’s what people repeatedly do when no one is telling them what to do. That means a culture concept has to be translated twice — first into mindsets people hold, then into behaviors people can see.

Take “listen and learn, not tell.” Before anyone can live it, they need answers to the questions this phrase doesn’t address:

• When a Schroders process differs from ours, is the default to adopt it, study it, or replace it?
• Who has the burden of proof when two ways of working collide?
• What does “listening” look like in an integration meeting versus a client handoff versus a technology decision?
• What happens to the person who says “that’s not how we do it here”?

Until those answers exist, the declaration is a sentiment. Sentiments don’t survive a deadline, a cost overrun, or a frustrated manager who just wants the systems unified.

Translating the declaration

This is what my Steering Guide framework is built to do. It starts with one Guiding Principle, the core trait that defines the organization. It translates that principle into Core Commitments, the universal mindsets everyone holds. Then it breaks down each commitment into Supporting Actions, written as “by [specific action], to [benefit].” The actions are the same for everyone. Each person applies them to their own role.

Here’s what that translation could look like for Huffman’s idea:

Core Commitment: Assume the other side knows something we don’t. The mindset shift is from evaluating the acquired company to studying it.

• By asking how a process works and why it was built that way before proposing a change, to make sure we don’t dismantle something that’s producing results.
• By documenting one practice from the other organization each month that outperforms our own, to make learning visible instead of assumed.

Core Commitment: Earn the right to change things. The mindset shift is from “we own it, so we decide” to “we change what we understand.”

• By presenting evidence of a problem before recommending a solution, to keep integration decisions grounded in performance, not preference.
• By naming what will stay the same when proposing what will change, to reduce the anxiety that makes good people leave.

Core Commitment: Protect what makes people effective. Huffman already practices this with portfolio managers. The mindset extends it to everyone.

• By asking a team what they need to keep doing their best work before restructuring how they work, to retain the capability we paid for.

None of these are slogans. Every one of them can be observed, coached, and measured. A manager can watch a meeting and know whether it happened. That’s the difference between a culture declaration and a culture.

The window is the work

Schroders will run as a separate company inside Nuveen for 12 to 18 months. After that, Huffman says, the two will figure out how they come together as something new.

That window is either the most valuable period of the integration or the most wasted. Separation protects people from disruption. It doesn’t teach them how to work together. If the mindsets and behaviors aren’t defined before the walls come down, they’ll be defined in the moment, under pressure, by whoever has the most authority in the room. That’s usually the acquirer.

The smart move is to use the separation period to translate the culture concept with people from both organizations, not for them. Bring leaders and front-line employees from each side together. Have them define what “listen and learn” looks like in their own work. Test the actions. Refine them. Then, when integration begins, everyone works from the same playbook rather than their own interpretation.

Say it, then spell it out

Huffman has the instinct most acquiring CEOs lack. He knows arrogance kills deals, and he knows the acquired company brings value worth protecting. That’s a strong starting point.

But a starting point isn’t a culture. Every leader who declares a culture is making a bet that people will interpret it the way they intended. That bet loses far more often than it wins.

If you want a culture, don’t announce it. Translate it. Define the mindsets. Spell out the behaviors. Make it the same for everyone, and let each person apply it to their own work. Otherwise, you haven’t built a culture. You’ve written a declaration.

Nuveen just closed its $13.1 billion acquisition of Schroders, the 222-year-old British asset manager. The deal pushes Nuveen into the top 10 global asset managers, with $2.6 trillion under management.

The headline is the money. The more interesting part is what CEO Bill Huffman said about culture. After more than 10 acquisitions, he has a clear view of how most mergers go wrong. The acquirer walks in, decides it knows better, and starts making everything its way. His alternative is simple. The first job after a deal is listening and learning, “Right? Not telling.”

He’s right. And it won’t be enough.

I never went to business school — but I have, on occasion, wondered how my life would be different if I had. Who would I have met? What advice would I have been given? What insights might I have uncovered with a little more guidance?

I have no regrets about the path I chose. I’ve always been comfortable with teaching myself and learning on my own time, so the B-school track never really felt right for me. I’m not alone — in 2023, less than 6% of entrepreneurs held an MBA. Still, that figure represents a 45% increase since 2010, meaning that overall, there’s far more demand for such degrees than in years past. 

Lately, I’ve been getting a lot of questions about whether business school is a good idea for aspiring entrepreneurs, especially in the age of AI. My answer? It depends on what you’re hoping to get out of it. 

What business school can give you

Experts largely agree that business school can offer you one thing that can’t be achieved via online tutorials: a large, built-in network. Not only will you be sitting in a classroom full of ambitious people, but you’ll also have access to faculty, guest lecturers and very likely, an expansive alumni network. These are the people you can call upon when you need advice, a warm introduction or feedback on your latest idea. 

It’s not part of the syllabus, but it is one advantage that comes up in nearly every discussion weighing the pros and cons of an MBA. Northwestern’s Kellogg School of Management, for example, has a global alumni network that spans 65,000 people across more than 15 industries, and other programs have similarly impressive reach. 

That said, a network is only what you make of it. Connections go cold if you don’t nurture them, and even the most impressive alumni directory won’t matter if you don’t pick up the phone. 

It’s also totally possible to create a network on your own. When I was building Jotform, I leaned heavily on a community I built the old fashioned way — through meetups, former colleagues and yes, alumni from my alma mater. It may have been a more painstaking process, but in the end, I felt I had the resources I needed. 

An expansive network has obvious benefits. The question is whether an MBA is the only way to get one, and whether the years and the tuition are the price you’re willing to pay for it.

Formal training vs. learning by doing

There are plenty of reasons why getting an MBA might seem like a good idea. Maybe you think having a degree from a top university is validating — or that investors will take you more seriously. Maybe you just like the idea of two years to think before the pressure of running something real sets in.

While there is merit to this thinking, none of that will actually get you any closer to building what you want to build, especially with price tags that can set you back $100,000 — or more — each year. (Though it’s worth noting that some schools are currently slashing fees to attract more students). 

Still, the parts of business school I wish I’d had before I started Jotform were the parts I had to learn from sometimes painful trial-and-error. Before I became a founder, I lacked even a basic knowledge of leadership, accounting or marketing. I was a coder, and that was pretty much it. 

I was lucky, though: As a bootstrapped founder, my mistakes were made on a relatively small scale. I grew slowly, which gave me time to hone my leadership chops gradually. Had I not gone that path, it’s entirely possible I’d have wished for more training. 

The fact is that nothing can really ever prepare you for starting your own business. An MBA can, however, help lay the groundwork.  

The role of AI

Had I had access to AI when I started my business back in 2006, things would have looked very different. Not in the fundamental sense — I still would have been a bootstrapped founder, and I still would have opted to learn-by-doing. But the learning curve would certainly have been less steep. 

Somewhat counterintuitively, I think this actually strengthens the argument for pursuing an MBA in the AI age. Good business schools are teaching students to think strategically and grow the soft skills that successful leadership demands. Case discussions force you to defend a position out loud, in front of people who will push back. Group projects teach you to manage disagreements. Those are muscles that need to be built, now more than ever. 

Networks can be built from scratch, and AI can certainly close many of the skills gaps a budding entrepreneur will need. If you’re on the fence, ask yourself why you’re doing it, and what you hope to gain.

I never went to business school — but I have, on occasion, wondered how my life would be different if I had. Who would I have met? What advice would I have been given? What insights might I have uncovered with a little more guidance?

I have no regrets about the path I chose. I’ve always been comfortable with teaching myself and learning on my own time, so the B-school track never really felt right for me. I’m not alone — in 2023, less than 6% of entrepreneurs held an MBA. Still, that figure represents a 45% increase since 2010, meaning that overall, there’s far more demand for such degrees than in years past. 

Lately, I’ve been getting a lot of questions about whether business school is a good idea for aspiring entrepreneurs, especially in the age of AI. My answer? It depends on what you’re hoping to get out of it. 

An email arrived this summer with the subject line “Magic Key Holder, your Magic Key pass expires in one month.” It invited me to renew before my expiration date of Sept. 17.

I’ve been a pass holder since 2018, first through the Annual Passport program and then through Magic Key, which replaced it in 2021. This past year I held the Inspire Key, the top tier, at $1,749. I’ve stayed at Disney’s Grand Californian. I’ve booked guided tours at both Disneyland and Walt Disney World. I’ve eaten and shopped in the parks.

I decided more than six months ago that I wasn’t renewing my pass. My last visit was December 20. I still love Disneyland, and I plan to go once a year with my parents.

The part of the email that stayed with me was the timing. It was tied to a date on my contract. It had nothing to do with anything I did or stopped doing. If they had solicited my feedback earlier and not just assumed I would renew my pass, they might have changed my mind.

In my work coaching tech leaders, I watch the same thing happen with feedback. Leaders build a feedback process, put it on a schedule and receive information too late to actually act upon it. Here are three timing problems to fix if you want honest feedback from your team while you can still use it.

Ask hard questions while plans can still change

One of my clients found out days before his latest product launch that his team wasn’t going to hit their deadline. He came to our session frustrated with them for not telling him sooner. I asked what he had done to create a way for them to tell him the launch was falling behind schedule.

He had been checking in, but the problem was when. He asked for updates late in the cycle — after the plan was already set — because that was his habit, and he accepted what he heard at face value because it matched what he expected. He didn’t give his team any other way to raise a concern before it became a crisis.

We changed his check-in cadence. He started checking in earlier, well before the plan was locked in, and he stopped assuming projects would take the length of time he had in his head, asking his direct reports directly instead.

Most of his launches have gone out on time since. For the ones that fell behind, he knew far enough in advance to get ahead of disaster.

More importantly, he avoided having to tell his executive team and the customer that he was going to be late, which was the part that frustrated him most.

Don’t make feedback a once-a-year thing

Years ago, a boss of mine asked our department to complete a written feedback exercise on every colleague. I was on my way out the door at the time, so I declined to participate. Formal feedback about people I was leaving, delivered in my final week, wasn’t going to change anything for them. I also didn’t want their last impression of me to be a critique that was headed for their employee file.

The exercise was reasonable. My issue was the timing, since the results would land after I was gone.

Annual reviews and exit surveys work the same way. If you wait until your staff submits a form in June or December, you’ll just get a summary of decisions people have already made, and you’ll have no way to change course.

You have to ask yourself whether what you learn will still change the outcome. When the answer is no, you’re just keeping records.

Set expectations before problems arise

Another client was promoted multiple times, from senior engineer to vice president. His title kept changing, but the way people treated him stayed where he started. He noticed it most when former peers, now his direct reports, kept taking questions to his boss instead of to him.

We decided that it was best for him to set up a series of direct conversations with each person now reporting to him. He opened with language like this: “I recognize our working relationship has shifted. In this capacity, I need to give you feedback as your manager rather than as a peer. How would you like to receive that feedback?”

Then he asked the reverse: How did they want to give feedback to him?

He did this before anything had gone wrong, which is what made it work. Sorting out how feedback moves between people is a much easier conversation when there’s nothing at stake.

Within a few months, his team was bringing issues to him first, instead of going to his boss.

Final thoughts on getting more honest feedback from your team

I tell my clients they have a choice: You can be frustrated that the feedback you want isn’t reaching you, or you can go get it.

Getting useful feedback means asking earlier and asking more often. Ask at a time when people can still act on what you say, then pay attention to what shows up. You’ve got this!

An email arrived this summer with the subject line “Magic Key Holder, your Magic Key pass expires in one month.” It invited me to renew before my expiration date of Sept. 17.

I’ve been a pass holder since 2018, first through the Annual Passport program and then through Magic Key, which replaced it in 2021. This past year I held the Inspire Key, the top tier, at $1,749. I’ve stayed at Disney’s Grand Californian. I’ve booked guided tours at both Disneyland and Walt Disney World. I’ve eaten and shopped in the parks.

I decided more than six months ago that I wasn’t renewing my pass. My last visit was December 20. I still love Disneyland, and I plan to go once a year with my parents.

Who can take a sunrise, sprinkle it with dew, cover it with chocolate and a miracle or two? The candy man can, and this time, the candy man is Kevin McCarthy, CEO of Unreal Snacks.

Kevin’s story is a great one for anyone who thinks they need the “right” résumé to succeed. He joined Unreal in 2014 at 22, fresh off a congressional campaign, with zero food experience. He was one of three employees. Today, Unreal is the largest better-for-you chocolate brand in America, sold in 35,000 stores across the U.S. and Canada.

Kevin joined me on How Success Happens (where I ate an embarrassing amount of peanut butter cups on camera), and I’ve broken down 5 bite-sized success tips from our conversation to help give your career a sugar rush.

Listen here

Subscribe now: Apple | Spotify | YouTube

Sometimes the Smartest Move Is Shrinking

Unreal launched in 2011 and exploded fast, but the infrastructure wasn’t there to support it. “The company used to be in 34,000 stores,” Kevin says. When he arrived, it relaunched in just 38. “We were trying to do way too much way too quickly, and we weren’t learning at an appropriate pace.” The fix was going small, nailing the basics, and climbing back one step at a time.

Takeaway: If growth is outpacing your learning, slow down until you’ve mastered a smaller version of your business.

The First Bite Is Your Real Marketing Plan

Kevin believes a healthier product only works if it delivers on pleasure. “The bite is the moment of truth,” he says. “When you have a big name like Unreal, you need to deliver on the taste.” That obsession drives Unreal’s high repeat-purchase rate, and its loyal customers have become what Kevin calls “the best marketing engine of anything.”

Takeaway: Before you spend a dollar on ads, make sure your product earns a second purchase on its own.

Subscribe to the free How Success Happens Newsletter for weekly inspiration.

Give Your Team a Perk That Makes Them Smarter

Unreal has an unlimited chocolate policy: employees can buy as much chocolate as they want, from Unreal and its competitors, then report back on taste and shelf presence. “We’ll do close to a ton of chocolate this year,” Kevin says. The result is lively internal debates, like testing thousands of samples to decide whether a peanut butter center should be gritty, crunchy or smooth. Everyone gets a voice, “but then we pick a path and we move forward.”

Takeaway: Design perks that turn your employees into sharper students of your market.

Good Surprises Are Dangerous Too

Kevin’s leadership philosophy centers on staying level. “You can never get too excited. You can never get too down.” He goes further: “I don’t like surprises that are bad. I also don’t like surprises that are good because we’re probably not prepared for them.” Landing a big retailer like Costco is worth celebrating, but it also means “now you gotta succeed.”

Takeaway: Treat every big win as the start of a new to-do list, not a finish line.

Think Massive, Act One Step at a Time

For the person in their kitchen whose friends keep saying “you should sell this,” Kevin says to start by being clear about who you serve and why your product is different. Dream about building a massive, well-loved brand, but be ready for the unglamorous work and the near-failures. “You’re gonna take step one, but there’s gonna be step two million someday down the road.”

Takeaway: Write down exactly who your product is for, then take the very next step toward reaching them.

Learn More

Load up on Unreal candy at unrealsnacks.com or at major retailers including Costco, Target and Whole Foods. And follow the brand on Instagram at @unreal.snacks.

Want to go deeper on the topics Kevin covered? Check out these stories on Entrepreneur.com:

About How Success Happens

Each episode of How Success Happens shares the inspiring, entertaining, and unexpected journeys that influential leaders in business, the arts, and sports traveled on their way to becoming household names. It’s a reminder that behind every big-time career, there is a person who persisted in the face of self-doubt, failure, and anything else that got thrown in their way.

Who can take a sunrise, sprinkle it with dew, cover it with chocolate and a miracle or two? The candy man can, and this time, the candy man is Kevin McCarthy, CEO of Unreal Snacks.

Kevin’s story is a great one for anyone who thinks they need the “right” résumé to succeed. He joined Unreal in 2014 at 22, fresh off a congressional campaign, with zero food experience. He was one of three employees. Today, Unreal is the largest better-for-you chocolate brand in America, sold in 35,000 stores across the U.S. and Canada.

Kevin joined me on How Success Happens (where I ate an embarrassing amount of peanut butter cups on camera), and I’ve broken down 5 bite-sized success tips from our conversation to help give your career a sugar rush.

One of the hardest decisions for entrepreneurs is not making a plan. Changing the business roadmap can feel like a loss of credibility. It’s admitting that a plan you believed in, invested in and asked your team to follow no longer makes sense.

To me, true business maturity is knowing when to let go of the original plan, adapt to changing circumstances and move forward in a new direction. Throughout my career running a legal consulting firm that advises fintechs on licensing and expansion, I’ve dealt with compliance every day. 

My experience has shown that regulatory developments can reshape the business landscape with little warning, and sometimes, growth begins with recognizing that the assumptions behind the original plan no longer hold.

It’s not an unusual challenge for business leaders. KPMG’s 2025 Global CEO Outlook reads that 72% of CEOs had already adjusted their growth strategies in response to interconnected challenges.

That figure doesn’t tell us whether those changes succeeded or whether the CEOs changed their ambitions. It does show, however, that revisiting a strategy is a familiar part of leading through uncertainty, not necessarily an admission that the original plan was badly conceived.

For fintech and crypto firms, the distance between a business plan and reality can widen rather swiftly. According to The Atlantic Council’s September 2026 tracker, digital currencies are classified as legal in 45 countries, partially banned in 20 and generally banned in 10. 

Consider a company preparing to enter a new market. It has budgeted for licensing, hired a local team and set a launch date. Then regulatory requirements change, banking partners become harder to secure, and the cost of entering the market rises.

The question is no longer whether the team can deliver the original plan. It is whether doing so still makes business sense. In an environment this fragmented and dynamic, I would start with a straightforward question: “Given what we know now, would we make the same decision today?” If the answer is no, it’s worth understanding why before committing further money or people.

Tweak your vision without losing sight of the goal

Changing a plan doesn’t mean you’ve given up on the objective. It might just involve postponing a launch, scaling back expansion spend, shifting focus to a different jurisdiction or narrowing the initial product to what the company can responsibly deliver.

I learned this firsthand when a geopolitical shift caused us to lose half our market virtually overnight. It was a stark reminder of how costly it can be to rely on a fixed roadmap because the plan was built for conditions that no longer existed. It reinforced a lesson I’ve carried into later decisions: Strategy needs room to adapt when circumstances change.

We still hold a five-year vision of where we want to be, alongside an annual plan that guides our priorities. We review our metrics and assumptions every month and conduct a deeper strategic review every three to four months. In some cases, we adjust these roadmaps even more often, because industry regulation moves faster than any planning cycle can keep up with.

My business decisions rest on concrete questions:

• Can we operate lawfully and sustainably in this market?
• Do we understand the full cost and likely timeline?
• Are qualified banking, payment and technology partners available?
• Can our teams support the expansion or restructuring without compromising existing customers?
• What evidence would make us confident enough to proceed?

They help me decide whether to move ahead, pause or change course, and stop “being cautious” from becoming an excuse to avoid making a decision.

The real reason changing a plan feels so hard

Changing course is also hard because clients, employees, investors and business partners may have already invested time, money and trust in the original plan. Changing direction means reconsidering not only your own decisions but also the commitments and expectations you’ve created for others. And this is exactly why it calls for honesty about uncertainty.  You simply need to explain what the company knows now, what remains unclear and what it will do next.

From a practical standpoint, your employees need to know what changes in their work, customers need realistic expectations, while investors and partners need to understand which risks the company is reducing and what conditions would justify resuming investment.

“We are delaying the launch because we cannot yet support it responsibly under the current conditions” is more helpful than a fog of corporate euphemisms. 

To make future course corrections easier, it’d be good practice to create habits that help the business respond well to whatever changes come next:

• Regular strategy and financial reviews: Put a monthly review of your finances, strategy and priorities on the calendar. Check whether the assumptions behind your plan still hold, and move resources when they don’t.
• Scenario planning and crisis preparedness: Think through the risks that could disrupt your business. Decide what you would protect, what you could pause and who would make the call.
• Build a culture of adaptability: Make it normal for people to raise concerns and question assumptions. You want to hear about a problem while you still have options, not after it has become expensive.

Ultimately, business maturity is not about sticking to the original plan at all costs. It is about understanding that a plan is a tool for reaching your goals, not a promise to ignore reality.

For entrepreneurs, real leadership means questioning their own assumptions, acknowledging when a strategy no longer works and changing direction when circumstances demand it. The responsibility of a leader is not to defend yesterday’s decisions, but to make the best possible decisions based on what they know today.

One of the hardest decisions for entrepreneurs is not making a plan. Changing the business roadmap can feel like a loss of credibility. It’s admitting that a plan you believed in, invested in and asked your team to follow no longer makes sense.

To me, true business maturity is knowing when to let go of the original plan, adapt to changing circumstances and move forward in a new direction. Throughout my career running a legal consulting firm that advises fintechs on licensing and expansion, I’ve dealt with compliance every day. 

My experience has shown that regulatory developments can reshape the business landscape with little warning, and sometimes, growth begins with recognizing that the assumptions behind the original plan no longer hold.

Most entrepreneurs have been told to “educate the audience.” It sounds right, since educated buyers make better decisions and useful content builds trust.

But a lot of educational content behaves like a textbook in a room full of people who came to make a decision.

Your audience isn’t opening social media for a lecture. They’re looking for signals. Should I buy now or wait? Should I hire the specialist or keep doing it myself? Should I follow the conventional wisdom or trust the contrarian take?

That’s why one of the biggest shifts we’ve made for clients is moving from “expert content” to what I call “decision content.” Expert content says, “Here is what I know.” Decision content says, “Here is how I would think about the choice you’re facing.”

In a recent campaign for a real estate client, we weren’t starting from scratch. The client already had what most professionals in the category lack: real local market knowledge, genuine investment experience and a clear point of view. The issue wasn’t a lack of expertise. Too much of the category sounds the same, with everyone explaining interest rates, neighborhood trends and generic buying tips.

So we stopped treating the content calendar like a list of topics and started treating it like a list of decisions. Instead of explaining a neighborhood, we framed the conversation around whether that neighborhood was undervalued. Instead of posting a broad investment tip, we turned it into a framework for spotting a good investment property. And instead of making a polite market observation, we created comparison content that helped viewers choose between two places, strategies, or assumptions.

The performance changed because the content asked the audience to participate. They could agree. They could disagree. They could imagine themselves making the same call. That’s the difference between content people scroll past and content they stop for.

From May through August, the organic campaign generated:

• 818,000 impressions
• 11,515 interactions
• 25% follower growth
• A top post that reached 48,000 impressions and drove 1,678 interactions on its own

The common thread wasn’t production complexity or a trend we’d copied. It was the framing. The highest-performing short-form videos helped people make sense of a real decision.

Here’s the framework we used, and how entrepreneurs in almost any industry can apply it.

1. Replace topics with tension

A topic is “how to choose a CRM.” Tension is “the CRM features founders overpay for before they have a real sales process.” A topic is “email marketing tips.” Tension is “why your best customers may not need another discount.”

Tension doesn’t mean being inflammatory. It means identifying the real trade-off your customer is weighing and naming it plainly.

2. Make your audience choose

People engage when content gives them a doorway into the conversation. “Here are three options” is fine. “Which of these three options would you choose if your budget were cut in half?” is stronger, because it gives the audience a role instead of a readout.

This matters most when your buyers are stuck between competing priorities: speed vs. quality, customization vs. simplicity, growth vs. margin and stability vs. experimentation. Your content shouldn’t flatten those trade-offs. It should bring them to the surface.

3. Use comparisons more often than explanations

Comparison is one of the cleanest ways to make expertise usable. “This versus that” forces specificity, and it mirrors how people actually buy, hire and invest. They’re rarely deciding whether a solution is good in the abstract. They’re deciding whether it’s better for them than the alternative.

A strong comparison doesn’t have to crown a universal winner. The best version explains who each option is right for, giving the audience a practical decision rule (way more useful than another list of tips).

4. Give your point of view before your proof

Many entrepreneurs pile on context, credentials and caveats before saying what they believe, and by the time the point arrives, the audience has moved on.

Decision content works better when you lead with your point of view. Say what you believe. Then explain how you got there. That doesn’t mean being careless with nuance. It means respecting the audience’s attention enough to lead with what matters.

Consider two openers:

• “I’d pay 20% more for a vendor who hits deadlines than save money on one who doesn’t.”
• “Price isn’t the only factor to weigh when comparing vendors.”

The first gives you an action to take while the second would still be true no matter which vendor you picked.

5. Measure the quality of the reaction, not just the reach

Views matter, but they don’t tell the whole story. Decision content often shows itself in the comments, saves, shares and messages that follow. If people are tagging someone, arguing with the premise, saving the framework or asking a follow-up question, the content is doing more than filling the feed. It’s helping the market think.

Many entrepreneurs make the mistake of believing they need more content ideas. Usually, they don’t. They need sharper decisions inside the ideas they already have.

If you sell software, stop explaining only features and start comparing moments when one workflow beats another. If you run a retail brand, stop only describing product benefits and start helping customers choose the right product for a real situation. And if you advise other businesses, stop only sharing best practices and start naming the tradeoffs leaders are afraid to say out loud.

The internet is overflowing with people who can explain things. Explanation is no longer enough on its own. The entrepreneurs who stand out are the ones who help their audience make a call.

Decision content works because it respects the real reason people pay attention. They’re not just collecting information. They’re trying to reduce uncertainty, defend a choice and move forward with more confidence.

So before you publish your next post, ask one question: What decision does this help my buyer make?

If the answer isn’t clear, the content probably isn’t either.

Most entrepreneurs have been told to “educate the audience.” It sounds right, since educated buyers make better decisions and useful content builds trust.

But a lot of educational content behaves like a textbook in a room full of people who came to make a decision.

Your audience isn’t opening social media for a lecture. They’re looking for signals. Should I buy now or wait? Should I hire the specialist or keep doing it myself? Should I follow the conventional wisdom or trust the contrarian take?