If you’re building a business in 2025, playing it safe is the fastest way to get left behind.

Having had a front-row seat to companies that have soared — and others that have stalled — I can tell you with certainty: Success rarely hinges on luck, timing or even market conditions. Those may influence the journey, but they don’t determine the destination. The biggest differentiator, time and time again, is bold leadership.

The founders who win aren’t always the smartest or the most well-funded. They’re the ones who move first, make decisions with conviction and aren’t afraid to break things in the pursuit of building something better. They lean into uncertainty instead of retreating from it. They execute while others analyze. Meanwhile, those who fall behind tend to hesitate. They wait for more data, better timing, clearer signals or external validation. And by the time they act, the window of opportunity has already closed.

In today’s climate, bold beats big. The environment is too dynamic and the competition too relentless for anyone to succeed by playing defense. The entrepreneurs who thrive are the ones willing to bet on themselves — and act like it.

Here are three bold moves we believe will define successful entrepreneurship in 2025 and beyond:

Related: The Benefits of Bold Leadership and How Leaders Can Develop a Bold Mindset

1. Make AI your co-founder

Most founders are still using AI like a toy — something to experiment with at the edges. The smartest ones? They’re going all-in, treating AI as a strategic co-founder baked into the core of their business model.

This isn’t about plugging ChatGPT into your website or automating customer support. We’re talking about AI-driven pricing models that adapt in real time, predictive hiring systems that flag your next top performer before they apply, autonomous lead scoring that prioritizes your highest-converting prospects and real-time behavioral analytics that anticipate what your customers want before they do.

This is about building an intelligent engine behind your company — one that gets sharper, faster and more insightful every single day. A company that learns while it grows. A business that doesn’t just scale but compounds.

Founders who embrace AI not just as a tool but as an operating system will outperform their peers on speed, precision and capacity. And in a world where the margin for error is shrinking, those advantages stack up fast.

Don’t wait for an AI playbook to be written. Write your own. Build with it now, or risk falling behind permanently.

2. Break the traditional funding playbook

The VC route has been glorified for decades. But in 2025, it’s no longer the holy grail, and it’s definitely not the only game in town.

More and more founders are rejecting the default path. They’re bootstrapping with profitability in mind from day one. They’re turning to equity crowdfunding to rally loyal customers into early investors. They’re experimenting with revenue-based financing, where repayment flexes with actual performance. Some are even exploring tokenized assets and community-led investment models that prioritize long-term alignment over short-term valuation hype.

This shift isn’t just about avoiding dilution. It’s about staying in control. It’s about building companies that reflect the values and vision of the founder — not just the expectations of a cap table.

In a world where capital is being democratized and distribution is increasingly direct, the most agile entrepreneurs are finding new ways to fund their growth, and they’re doing it without giving up the steering wheel.

If your funding source controls your destiny, then it’s not really your company. Rethink your capital stack with the same creativity you bring to product and brand.

Related: 5 Risk-Taking Lessons From Founders Who Bet Big and Won

3. Rethink your end game — now

Most founders start with a product idea. Fewer start with a clear vision of where they want the journey to end.

That worked in an era of frothy markets, where acquisition offers flowed and IPOs were aspirational but attainable. But we’re not in that era anymore. Capital is tighter. Buyers are more disciplined. And exits don’t just happen — they’re engineered.

If you want freedom later, get intentional now. Whether your goal is to build a sellable company, transition to private equity, create a long-term cash-flow machine or step away entirely and let the business run without you, you need to reverse-engineer that path from the start. Your endgame should shape everything from your hiring strategy to your operating model to your pricing.

Running a business without an exit strategy is like setting sail without a destination. You’ll work hard, but you might not end up anywhere that matters.

Design with the end in mind, and don’t be afraid to challenge what “success” is supposed to look like.

Related: Make That Bold Move Now — and Avoid Looking Back With Regret

Entrepreneurship in 2025 doesn’t reward hesitation. It rewards courage, clarity and a willingness to make bold, sometimes uncomfortable decisions — long before the market tells you it’s safe to do so.

The founders who thrive in this era won’t be the ones who waited for permission. They’ll be the ones who acted with urgency, redefined the rules and built businesses that reflected the future, not the past.

Still playing by the old rules?

Your competitors hope you are.

Ready to break through your revenue ceiling? Join us at Level Up, a conference for ambitious business leaders to unlock new growth opportunities.

A typical supercommuter spends 60–90 minutes or more one way commuting to work or school. As the cost of living continues to outpace wage growth, supercommuting is growing in popularity. According to a recent U.S. Census Bureau report, an estimated 5 million people are now supercommuters—up from roughly 3.42 million in 2012.

I hate long commutes. Taking the bus or driving to work was one of my top three annoyances while I was employed.

When I retired in 2012, one of the greatest joys was never having to commute again. Getting back that time, energy, and mental clarity was a truly lifestyle-enhancing benefit of retirement. Then, when the pandemic hit in 2020, millions around the world got to experience that same freedom. Is there any wonder why it’s been so hard to convince workers to go back to the office?

In this post, I want to highlight the hidden toll of supercommuting to work or school. Sure, you’ll spend more on gas if you drive. But that’s just the beginning. So before you buy a more affordable home in exchange for a longer commute, be forewarned: the trade-offs may not be worth it.

My Experience With Supercommuting

After deciding not to pony up a small fortune for a vacation rental in Honolulu, I opted for my family of four to stay with my parents for up to five weeks. They have three free bedrooms in their five-bedroom house, and it’s a home I’ve returned to for 39 years. It feels comfortable to me, but not to all.

Some of you thought this was a good way to save money. Others—mostly women—said it was cruel to subject my wife to such confinement for so long. I get it. Staying with your in-laws for more than a few days is a lot to ask, especially without en suite bathrooms or separate kitchens and entrances. And not everybody likes to be in Hawaii during the summer heat.

Still, the cheapest suitable three-bedroom rental I could find cost $16,000 after taxes and fees. A nothing fancy four-bedroom rental, without a pool, which we liked, was $24,000. After owning real estate since 2003, I just can’t bring myself to spend that much on a temporary stay that builds no equity.

To find a compromise, we stayed at my aunt and uncle’s place on the North Shore—up to 1.5 hours away—after 13 days with my parents, to give both my wife and mom a break for nine days. It gave me a break too as I could return to living without worry of doing things in a way that would displease my mom, e.g. cut fruit on the right side of the sink instead of the left.

The kids were happy wherever they were, so everyone won, well, except for me who had to drive ~2.5 more hours a day for five days.

The False Start

We picked up our kids at 4:55 p.m. Friday from summer school at Punahou to head to Laie for the weekend. All was well—until six minutes in, our five-year-old daughter announced she had to pee. I turned around and went back to school so she wouldn’t have to hold it.

Had we been commuting from my parents’ house, just eight minutes away, I would’ve just kept driving. That’s one unexpected cost of supercommuting—having to manage bodily functions mid-ride. Most adults can uncomfortably hold it for an hour or two. But kids? Not so much.

We finally arrived in Laie an hour and 25 minutes later. The kids napped for 35 minutes, so the trip felt like a breeze to them. Although I was tired, I was also excited to enjoy the freedom of having our own space again.

The Monday Morning Supercommute

After a fun weekend filled with Pokémon Go Fest, Giovanni’s garlic shrimp, and beach walks, reality returned Monday morning.

I passed out by 10 p.m. Sunday after putting the kids down by 9:20. I woke up at 2:45 a.m. to get a head start on publishing a new post, responding to comments, and going for a morning walk on the beach.

The kids woke up at 6:30 a.m., and we left by 6:55 to make it to school by 8. Back in Honolulu, we usually leave at 7:40, so the earlier start was a shock for my wife and daughter, who aren’t morning people.

Right away, I could tell the drive would take longer than expected. We were stuck behind a gasoline tanker on a single-lane road for about 15 miles, averaging just 32 mph instead of the usual 40–45.

About 45 minutes in, I got a text from my wife thanking me for the ride and the peace and quiet. At a stop light, I couldn’t help replying with a GPS screenshot to show where we were—7 minutes behind schedule. Usually, the GPS arrival time was conservative and easy to beat.

But then I made a mistake. I resumed driving while glancing at the screenshot I had sent her instead of the live Apple Maps. That brain fart cost us another 11 minutes. Instead of arriving at 8:05 a.m., we got to school at 8:16. Ugh—I hate being late.

A Place To Hang Out Made Supercommuting More Manageable

At first, I thought I’d just hang out at the beach or mall all day before picking the kids up at 4:55 p.m. My wife also wanted me to pick up some groceries. No problem. There was no way I was going to drive 1.15 hours back to Laie after drop off and then do it again in the afternoon. I figured I’d nap in the car under a banyan tree if I had to.

Then I remembered my parents’ house was only 8 minutes farther. I could write, rest, and manage the renovation of an in-law unit I was working on. Having a home base made the day much more manageable. If I had to also work a full-time job during that commute, I would’ve been completely wiped.

In fact, after dropping off the kids, I spent the day in the city writing a post, recording a solo podcast episode, talking to my parents, grabbing lunch, and squeezing in a quick 15-minute nap.

Then I dealt with the handyman, swung by Whole Foods for groceries, and picked up the kids at 4:55 p.m. The day flew by—and by the end of it, the thought of driving 1 hour and 15 minutes back to Laie was the last thing I wanted to do.

The Next Day of Supercommuting (Good Then Bad)

By the second day of supercommuting, I felt more confident. I knew the route better and had learned from my mistakes. I got the kids to school 10 minutes early and shaved 20 minutes off the drive. It felt like a small win. But of course, good things never last.

When I arrived at my parents’ house—another 10 minutes from school—the plumbers had already shown up early. Then, 30 minutes later, the handyman arrived. In total, I spent nine hours managing five different workers trying to fix up our long-neglected in-law unit. I hate remodeling and swore to never do so again. But here I was, like a masochist, doing it again while I was supposed to be on vacation. If I didn’t lead the charge, nobody would, as the place has been neglected for over five years.

To make the most of the downtime, I brought my laptop outside and worked on a new post. But with the sun blazing and temps hitting 85 degrees, I was drained by mid-afternoon.

By 4:40 p.m., all I wanted to do was lie down in an air-conditioned room and take a nap. But no such luxury. I had to hop back in the car, drive 10 minutes through rush hour to pick up the kids, then endure another 1 hour and 10 minutes back to Laie.

My zest for life? Gone. After 10 minutes of small talk with the kids about their day, I turned on some music and just listened like a zombie. I didn’t have the energy to keep the conversation going.

By the time we got home, I was toast—just a tired, slightly grumpy dad who wanted nothing more than to kick back and crack open a cold beer.

Positive Thoughts To Gut On Through

Even though I was commuting about 2.5 hours extra a day, I told myself it was worth it—for my wife’s sanity, my mom’s peace, and even my kids’ resilience. Maybe the longer commute would build their endurance and teach them the value of waking up early.

Perhaps most importantly, my wife appreciated the effort I put in to make her happy. Judging by her FaceTime calls from the beach, she definitely seemed more relaxed and content! With appreciation, I’m happy to keep on supercommuting.

As a father, you do what you can to provide. A little extra effort plus some problem-solving goes a long way to making a suboptimal situation better. Got to think positive!

Besides, knowing the supercommuting stint was temporary made it tolerable. My kids had Friday off for the 4th of July, so I only had to supercommute for four days—a total of ~11 hours of additional driving.

The Hidden Costs of Supercommuting

At first glance, supercommuting might seem like a reasonable trade-off. Save 20–60% on housing and spend an extra two hours and thirty minutes commuting a day? Maybe not so bad, especially if the median home price is above $1 million.

But in addition to hundreds more in gas and transit costs each month, here are other downsides:

• Increased risk of injury or death – More time on the road means more exposure to accidents, especially when driving with kids. I literally saw a car on a residential street near my parent’s house flip upside-down because it got t-boned at an intersection. One of the cars didn’t stop at the stop sign.
• Higher stress and cortisol levels – Bad drivers, traffic jams, and road rage add up, draining your emotional reserves for the day and evening. You might end up developing chronic pain, raise your stress levels, and ultimately, shorten your lifespan as a result.
• Wear and tear on your vehicle – More miles mean more maintenance, especially if your car isn’t ultra-reliable. For example, changing four tires on my Range Rover sport costs $1,650, and they only last about 16,000 – 18,000 miles.
• Greater chance of getting tickets – From parking mistakes to speeding tickets, increased driving time raises your chances of infractions. In turn, your car insurance premiums could go up.
• Reduced happiness and harmony with your significant other – Long commutes drain your energy and patience, which means by the time you get home, you might be more irritable, checked out, or just plain exhausted. Small disagreements can flare up more easily when one or both of you are running on fumes. Over time, the emotional toll of being physically distant and mentally unavailable adds up.

If You Are Going To Regularly Supercommute

If you plan to supercommute regularly, two things are imperative: a safe, reliable car and life insurance.

My wife and I have matching 20-year term life insurance policies, which have provided tremendous peace of mind. I recommend locking in an affordable policy through Policygenius to cover your debts and protect your children until they become adults.

Here in Honolulu, however, we don’t have what I’d consider a safe-enough car for long-term supercommuting. We’re using my dad’s 1997 Toyota Avalon. While it’s a nostalgic beast, it has poor acceleration for evasive driving, a wobbly axle, shaky brakes above 45 mph, no side curtain or rear airbags, no blind spot detectors, no sensors, and no rear camera. I’m not even sure the front airbags work—my guess is they haven’t been replaced since he bought the car.

As a result, I drive slowly and try to stay extra alert. The one saving grace is that the speed limits between the North Shore and Honolulu are relatively low—35 mph on the single-lane “highway” and 50 mph on the main freeways. So it’s not like mainland highways where people routinely push 70–85 mph.

If we return to this same living and commuting arrangement again, I plan to rent a new car. It’ll not only be safer, but it’ll also free up my dad to run errands during the week with his own 28-year-old car. A win-win.

Final Thoughts on Supercommuting

Supercommuting might seem like a smart financial move, especially when housing near work is unaffordable. But before you commit, look beyond the savings. Living in a smaller house or apartment to save time commuting is my preference .

Every hour on the road is an hour not spent with your loved ones. Every stressful drive takes a toll on your mood, focus, and health. And every unexpected delay chips away at your patience—especially when you’re juggling the demands of family life and work.

For me, those long drives were about more than transportation. They were about making a tough situation work, even if only temporarily.

If you’re going to supercommute, have a plan. Know your timeline. Understand your reasons. And make sure the trade-off is truly worth it. Because in the end, a cheaper home isn’t worth it if it leaves you drained and hating life.

The Value of a Well-Located Home

Personally, a comparable home would need to be at least 75% cheaper to justify adding two extra hours of commuting each day. And even then, I’m not sure the trade-off would be worth the toll on my time, energy, and well-being. The time I get to spend with my kids after school is simply too precious to sacrifice.

If you live within 15 minutes of both your work and your children’s school, consider yourself fortunate. While remote work surged during the pandemic, in-person collaboration has made a strong comeback. As a result, well-located homes in job-centric cities—especially where supply is constrained—may outperform in the future.

When my children’s school moved in 2024, our drop-off time shrank from 15 minutes to just 8. That may not sound like much, but it’s been a noticeable quality-of-life upgrade. Now, if I need to swing by school to drop off lunch or attend an event, it’s a quick and easy trip.

Of course, if I had to commute downtown daily, the drive would stretch to around 25 minutes, or 25 minutes by MUNI, including walking to the station—just beyond my ideal maximum for a work commute. Fortunately, we don’t have to go into an office anymore. And for that, I’m especially grateful.

Readers, are any of you supercommuters? If so, how do you make the long transportation time more bearable? Are there any unexpected benefits to supercommuting beyond saving on housing costs or being closer to family or a better school? I’d love to hear your strategies and insights.

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Barbara Corcoran, the 76-year-old founder of the real estate firm The Corcoran Group, claims to have created a work environment where there was “no turnover.”

In an Instagram post shared with her 1.2 million followers on Monday, Corcoran outlined the “crazy things” she would do to keep her staff happy. For example, Corcoran would bus hundreds of agents to the country for midweek picnics, each with its own memorable feature, like a 60-foot-tall hot air balloon or a 5,000-pound elephant offering safari rides.

Related: Barbara Corcoran Needed to Make Job Cuts. Here’s Why She Fired Her Mom First.

She would also provide babysitters for employees who wanted to bring their kids to work and offered plenty of office perks, like yoga classes, free lunches, and massages.

Corcoran recognized top performers by giving gold ribbons to anyone who closed a million-dollar sale, and gave one of her top brokers a Bentley with the license plate “SOLD1” to highlight her stellar performance in front of the whole company.

She additionally claims to have thrown “the wildest parties in town” for her employees, complete with their own “wacky” themes — and dressing up was mandatory.

The end result of these initiatives? People were “lining up” for jobs at The Corcoran Group, and Corcoran didn’t have to advertise new job openings. There was also zero turnover; employees chose to stay.

Related: ‘Do You Know What a First Class Ticket Costs?’ Why Barbara Corcoran Flies Coach

“People are most creative when they’re having fun, and we had more of that than anyone else,” Corcoran wrote in the post. “I stopped advertising to hire because people were lining up to work at The Corcoran Group! Fun builds loyalty, and we had no turnover.”

Corcoran founded The Corcoran Group in 1973 with just $1,000 and seven agents. By the time she sold the brokerage firm for close to $70 million in 2001, the team had grown to encompass 700 employees.

Corcoran also noted in an Instagram video in March that she is “the best boss” she has ever met because she follows a simple principle: She works for whoever works for her. In other words, she works for her employees, and her perspective is always tied to what she can do for them.

“I shower my people with anything they need selflessly,” Corcoran said in the video, adding later that, “I don’t think anyone could be a better boss than me.”

Corcoran is now an original cast member of “Shark Tank.” She has appeared on the show for 16 seasons and made more than 650 deals. She makes about $4.5 million a year from her investments, including profits from deals from the show.