February 2025

Citigroup made the mistake of crediting $81 trillion to a customer’s account instead of $280, according to a Friday report from the Financial Times.

The multi-trillion-dollar error occurred in April 2024 and was overlooked by both a payments employee and a second employee assigned to check the transaction before it was approved to be processed. A third employee caught the mistake 90 minutes after the payment was posted, leading Citigroup to reverse the transaction several hours after it had been submitted, per the outlet.

The value of the transaction far exceeds the gross domestic product of every country in the world, including the $29.72 trillion GDP of the U.S. It also surpasses Citigroup’s own $147 billion market capitalization.

No funds left the bank. Citigroup disclosed the “near miss,” or the term for a bank processing a wrong amount but recovering the funds, to the U.S. Federal Reserve and the Office of the Comptroller of the Currency.

Related: Citigroup Is Sticking With a Hybrid Work Schedule. It Gives the Bank a Competitive Advantage, According to Its CEO.

A Citigroup spokesperson told Business Insider that the incident was an “inputting error” and that there was “no impact to the bank or our client.” They also stated that the transaction was so large it could not have been processed.

“Despite the fact that a payment of this size could not actually have been executed, our detective controls promptly identified the inputting error between two Citi ledger accounts and we reversed the entry,” a Citigroup spokesperson told BI.

The bank also told the FT that it would push to eliminate manual entry and work on automating the inputting process.

^{Citigroup CEO Jane Fraser. Photographer: Paul Yeung/Bloomberg via Getty Images}

This isn’t the first time Citigroup has made a massive inputting error. FT reported that 10 near misses of $1 billion or more occurred at Citigroup last year, down from 13 cases in 2023.

In August 2020, Citigroup accidentally sent $900 million to the creditors of cosmetics company Revlon instead of a $7.8 million interest payment. It took the bank two years of legal action to recover most of the money. The episode led to the early retirement of then-CEO Michael Corbat and a fine of $400 million from U.S. regulators over “unsafe and unsound banking practices.”

Citigroup’s current CEO, Jane Fraser, stated when she was named to the CEO role in September 2020 that she would work to ensure that employees “operate in a safe and sound manner” by investing in infrastructure, risk management, and controls.

Two years later, a Citigroup employee accidentally added an extra zero to a trade, sparking a stock selloff that wiped out about 300 billion euros, or $322 billion, from European stocks. British regulators fined Citigroup about 62 million pounds, or around $78 million, over the issue last year.

Related: Citigroup Eliminated More Jobs This Week. Here’s Which Roles Were Affected.

U.S. regulators also fined Citigroup $136 million last year for not correcting gaps in operations.

Citigroup isn’t the only major bank that has incurred fines over operations. JPMorgan Chase, the largest bank in the U.S. with $3.9 trillion in assets, was fined nearly $350 million in March 2024 by U.S. regulators for operating trades “without adequate oversight.”

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StackSocial prices subject to change.

This as-told-to story is based on a conversation with GumGum Advertising CEO Phil Schraeder, who’s had a successful side hustle appearing as a contestant on game shows. The piece has been edited for length and clarity. 

I’m originally from a small town outside of Chicago. My brother, sister and I were on the swim team in the summers, which meant early 6 a.m. mornings. This was back in the ’80s, where after swim practice, you’d go outside and play with your friends until dark, but in the mornings, no one else was awake. So, when we got home from swim practice around 7:30 a.m., my mom would make us breakfast and put on the TV — and my siblings and I would watch game shows.

I became fixated on those game shows, ones like The Price Is Right and Sale of the Century, and I’d play them with my siblings. I’m super competitive. I love trivia and winning prizes.

Related: ‘Jeopardy!’ Champion Buzzy Cohen Reveals 5 Surprising Parts of the Game Show That You Don’t See on TV

Fast forward to after I graduated from college: I worked in Chicago for a short time before deciding that I needed to find myself. I wanted to come out of the closet. I felt very held back from my authentic self. I wanted a change, so I moved with a friend to Los Angeles.

When I arrived, all I had was my car and what I could fit inside of it. I had no job, and I was in credit card debt. I needed to figure out a way to earn money. Luckily, I’ve always been focused on accounting and finance. My background is in business. So, I wasn’t worried about being able to find a job, but I still needed a way to make ends meet in the short term.

That’s when I started a fun and unique side hustle: competing on game shows. I ended up going on The Price Is Right with Bob Barker — and won. I walked away with $900 in cash, an amusement park popcorn cart and a grandfather clock. I was like, Wow, this is incredible. Not only did I love the experience, but I was also living out my childhood dream. I also loved knowing that my family was able to enjoy watching me do it.

Related: I Made Over $400,000 From a Side Hustle on Top of My 6-Figure Salary Last Year. I Love Diversified Income — and This Game-Changing Money-Saver.

Even as I progressed in my finance career, ultimately becoming a VP, I continued with the side hustle and kept a pulse on game show opportunities. Because Los Angeles is the entertainment capital of the world, a lot of first-time game shows have their start there, and they look for contestants locally. So, it’s not that competitive to apply; it’s not a nationwide search.

When I heard about the new show Are You Smarter Than a 5th Grader?, I knew I wanted to apply. And, being a 29-year-old finance and business accounting professional from Chicago, I provided an opportunity for them to try out a contestant who wasn’t in the entertainment industry. Still, it was a long audition process. But I was invited on the show and given about 10 days to prepare.

I wasn’t going to squander the chance. I went to the kids’ homeschool store, and I bought all the third, fourth and fifth-grade books. I bought world geography. I bought measurements. I bought flashcards of the presidents. Every day after my life partner Wes and I woke up, I would study, then go to work. On my lunch break, I would study more. Later in the evenings at home, I’d study until I was falling asleep on the couch.

I ended up winning $175,000 on the show. It gave me a lot of financial freedom.

Related: Two Knicks and a Businessman Walk Into a Studio — And Turn Their Side Hustle Into a Booming Business. Here’s How They Did It

This side hustle provided other exciting chances to make money over the years. I also appeared on the Dick Clark Pyramid Show, where I won $22,500. I literally took the day off work, called my brother after I won and said, “Oh, that was a good day of work.”

But this sort of side hustle comes with some limitations, too. You can only go on so many game shows over the course of 10 years. Now, if the right opportunity presented itself, I’d consider taking it. I still love game shows and appreciate that they helped set me up financially, but at this point in my life, I’m in a different situation, so if I were to appear on one and win, I’d likely donate the money.

My game show side hustle definitely helped shape me as a business leader.

In the beginning, I was afraid that I might not be taken seriously as a seasoned executive business professional in finance because I enjoyed competing on game shows. But those were my own ideas about societal expectations and being boxed in, and it actually helped me realize that as a CEO and leader myself, I don’t want anyone to feel that their interests or side hustles negatively influence how they’re perceived professionally. We want to celebrate those interests and side hustles; we want to encourage them.

At GumGum, we’re in 20 countries and have over 500 people, so I’ve implemented what I call “starting classes”: whoever started in Q1 of this year would be in the Q1 2025 starting class. And I ask them a lot of questions. What are some people’s side hustles? What are they interested in? It’s amazing to watch everyone light up. There are DJs, macrame crafters, influencers and opera singers. Then, I think about how we can translate those passions into our culture and encourage and support each other in the community.

Related: How to Balance a Full-Time Job With a Side Hustle

From my experience on Are You Smarter Than a 5th Grader? in particular, I learned the value of listening to yourself and following that instinct. I was in a situation where I was unsure of the answer and had to decide if I wanted to risk it all and go with the kid’s answer. If the kid’s answer was correct, I could have won $300,000, but if it were wrong, I would have dropped down to $25,000. Since the kid wasn’t certain about the answer, I stuck with my own and kept the $175,000.

As it turned out, the kid’s answer was right, so I would have won $300,000. But it was still an important lesson in listening to myself — because although it would have felt great to win $300,000, it would have felt far worse to lose $150,000. In the end, I was completely fine with not winning more in order to protect what I already had. You need to stay true to what works for you and what you are comfortable with. Don’t think about what others might have or do, and then compare yourself.

My game show side hustle also taught me a lot about my personal motivations — and how those values can translate to leadership.

On Are You Smarter Than 5th Grader?, I received a surprise video message from my mom, who is an educator and my fifth-grade teacher. I get emotional on the show because my mom’s wishing me good luck. That moment made me realize that, yes, this is super fun, but whatever this is, it’s nothing compared to how lucky I am with the other aspects of my life. It reaffirmed what really matters.

Related: I Turned My Side Hustle Into a Passive Income Stream That’s Earned More Than $1 Million — But Making Money Isn’t Even the Best Part

When it comes to business, the most successful leaders are going to be the ones who can go very deep in humanizing us and themselves. I try to stay away from encouraging leaders to be “authentic” because the opposite of that is “inauthentic,” and I don’t think people try to show up inauthentically. They’re just trying to be more transparent.

So that’s my one big push, especially as it relates to the advertising industry: If you’re a leader in this field, the ultimate goal is connecting with someone deeply on an emotional level or a needs level. The best leaders need to show up prepared to do that every day.

As of Thursday, Meta has fired around 20 employees for spilling “confidential information” to the press and other parties outside of Meta.

“We recently conducted an investigation that resulted in roughly 20 employees being terminated for sharing confidential information outside the company, and we expect there will be more,” Meta spokesperson Dave Arnold told The Verge. “We take this seriously, and will continue to take action when we identify leaks.”

Arnold said that when employees join Meta, they are made aware of the company’s strict no-leaks policy, which prohibits staff from revealing internal information.

Related: ‘There Are Repercussions’: Meta Reminds Staff of Its Strict No-Leaks Policy — That Has Since Been Leaked to the Press

Meta cracked down on leaks after Meta CEO Mark Zuckerberg held an all-hands meeting last month — and a recording leaked to multiple outlets almost immediately. That same day, The Verge also obtained an internal memo sent to staff by Meta’s Chief Information Security Officer Guy Rosen warning them against sharing confidential information.

During a company Q&A earlier this month, Meta CTO Andrew Bosworth noted the “tremendous number of leaks” from inside the company and warned employees that Meta was “making progress on catching people.” A recording of the meeting also leaked to the press.

Related: Meta Confirms It Is Doubling Executives Bonuses to ‘Motivate’ and ‘Reward Them’ a Week After Layoffs

Meta conducted performance-based layoffs on February 10 that affected 5% of its 72,000-person workforce or about 3,600 employees who weren’t meeting standards. The cuts surprised some affected workers, who said they had a “solid” track record of performance at the company.

Meta has also recently made sweeping changes to how content is moderated on Facebook, Instagram, and Threads with the decision to roll out Community Notes, a system that enables users to flag misleading content and write explanations citing their sources. The new system replaces the independent fact-checking one that Meta had in place for eight years.

^{This article originally appeared on Business Insider.}

This as-told-to essay is based on a conversation with Jade Bonacolta, a 31-year-old in Miami who began her career at LinkedIn and is now the head of North American marketing at Google. Her employment and promotion history have been verified by Business Insider. The following has been edited for length and clarity.

After graduating from Columbia University in 2015, I landed a job at LinkedIn in San Francisco.

During the six-and-a-half years I was at LinkedIn before joining Google in 2022, I was promoted five times, beginning as an associate in the Business Leadership Program and leaving as the head of marketing for enterprise technology.

A lot of my promotions came from the way I handled my one-on-one meetings with my manager.

Preparing pre-reads for my one-on-ones

Most people go into one-on-ones taking a more passive approach, expecting their manager to present to them and tell them what to do. But managers often have teams of five or more people, so having weekly meetings with each of them can be a lot to juggle.

I noticed that my first manager would generally ask me the same things in every call — “How did this week go? What are you working on next week and where do you need help?” I knew I wanted to be more proactive and make those meetings more efficient.

I began spending an hour beforehand writing up what I called a “pre-read.” I would draft a simple email with three sections: what went well for me this week, what I’m focusing on next week, and one new idea or interesting innovation to suggest for our team.

I would send it to my manager before we met and bring my copy to the meeting to help guide our conversation.

My manager told me he found the pre-reads incredibly helpful; they made our conversations far more productive and helped him feel completely aware of my work. He found the format so useful that he asked the rest of my team members to follow the strategy for their one-on-ones as well.

3 things that make an effective pre-read before a 1:1 meeting

1. What went well

First, I created a “wins” folder, and every time I had a win throughout my week, I would add it to the folder.

For example, if, when working with the sales team, I received an email from one of the leaders saying, “I am so impressed with the questions you asked my team and the way you provided value,” that email would go straight into the wins folder. I would then pull from that folder when making my pre-read email to my manager.

I understood that I could be doing the best work in the world, but it didn’t matter if the right people didn’t know about it; if I wanted to be promoted, I needed to be visible.

I’d also save all of my wins in a document and share it with my manager to make it easier to write my performance review and build a case for my promotion.

2. What I’m working on

Managers are often expected to tell their employees what they should be working on. However, it can also be helpful and beneficial if the employees show proactiveness.

After sharing what I did the week before, I would then say, “Here’s what I think I should work on next week.” Some of these were ongoing projects, while others were new initiatives I was introducing.

When it came to projects, I had a pretty strong instinct on the direction I wanted to take my career, and I made the promotion I wanted clear to my manager. I asked them, “Are there any projects I could work on that allow me to start building those skills?”

I also tried to anticipate where I might need my manager’s help. I’d ask myself: “What could possibly go wrong next week?” and “Which person do I need to connect with next week that I might need an introduction to from my manager?”

This way, I could ask my questions all at once in the meeting rather than throughout the week.

I also tried to proactively come up with solutions, rather than just present problems.

For example, I might say to my manager, “It seems like we have to get our budget in by this date, so is there a way that I can submit this earlier this week in order to make sure that that deadline doesn’t sneak up on us?”

3. One new idea

In my pre-read, I’d also share one new idea.

Throughout the week, I would pay attention to things that my manager found frustrating or inefficiencies that came up over the past week — things that had simple fixes.

Then, in my one-on-one meetings, I’d offer an idea or solution to solve those issues. I realized that the ideas didn’t have to be big. In fact, when presenting a new idea, the key is to make it small, as you don’t want to take on an unhealthy amount of work and burn out, or neglect the main parts of your job.

Once, my team and I were doing really great work, but no one in our broader organization knew much about it. As I wanted to lean more into the marketing world, I asked my manager, “What if we started a very quick, regular newsletter?”

My manager agreed.

I took on ownership of that newsletter. Every month, I consolidated and sent out the newsletter to the entire organization, sharing updates on what our team was doing. It was simple, and other teams weren’t doing it, and I was reaching the leaders of other teams.

When those leaders would reach back out to my manager about how the newsletter was great, my manager would respond: “It was actually her idea. I didn’t even ask her to do that; she just volunteered to take this on.”

Spending an hour to prepare was worth it to give my manager visibility

I’ve repeated this process in every new role I’ve taken and every new manager I’ve had at Google. My managers have loved it, and I’ve received incredible feedback whenever I’ve done it.

Even in my now senior-level role, my leadership team deeply appreciates my weekly status updates and new ideas for the team. They treat me as a thought partner rather than just a direct report.

Making the most of one-on-one meetings gives your leaders more visibility into all the work you’re doing.

The first time I considered dismantling a perfectly functional product line, I hesitated. It felt reckless, maybe even self-sabotaging. But looking back, it was one of the most strategic moves I ever made. By deliberately engineering a controlled crisis within my organization, I uncovered an unexpected wellspring of innovation, resilience and growth. Rather than waiting for external forces to shake our foundation, we chose to preempt disruption — and the results changed everything.

Throughout my career leading organizations through transformational change, I’ve learned one counterintuitive truth: waiting for a crisis to drive transformation is a losing strategy. I’ve lived through more major disruptions than most executives see in a lifetime — from 9/11 and SARS to the 2008 financial crash and the global pandemic. Each time, I watched organizations struggle to react, their carefully crafted crisis management plans falling short of the moment’s unique demands.

What I observed time and again was that no matter how well-prepared an organization thought they were, these external shocks paralyzed people and systems. The recovery time was always longer than necessary, and the costs — both financial and human — were inevitably higher than they needed to be. We’d look back after each crisis and say, “If we had just made those changes sooner, we would have been better positioned.” The hard truth is that most organizations know what changes they need to make. They just lack the urgency to make them until external forces leave them no choice.

This pattern led me to a radical conclusion: what if, instead of waiting for disruption to happen to us, we created it ourselves? What if we looked at our business model every day and asked, “How could this be destroyed by competitors, market shifts or innovation?” It’s a scary question, but far less scary than facing those threats unprepared. When you’re running a mature business, it’s dangerously easy to get comfortable — to become the big fish that stops evolving because you think your position is secure.

Strategic foresight: Identifying where to strike

Opportunities to self-disrupt often hide in plain sight. They might be legacy products that have grown stale, processes that no longer scale effectively, or supply chains that lack flexibility. Strategic foresight means looking beyond immediate KPIs and asking tough questions about where the business might fracture if external pressures intensify.

• Are there product lines that consistently perform but show no real growth potential?
• Are we too dependent on a single vendor, region or technology stack?
• Have we locked ourselves into legacy models that hinder agility?

By mapping out these weak spots, leaders can anticipate where external disruption might strike and then move first — shattering old assumptions before competitors or market conditions do it for them. According to McKinsey, organizations that identify potential market inflection points ahead of the curve tend to outperform industry peers. Foresight isn’t just a forecasting exercise — it’s a strategic guardrail.

Related: How to Spot Trends and Anticipate Market Shifts Before Your Competition

Building resilience through controlled disruption

The question I hear most often is: “How do you create intentional disruption without destabilizing the entire organization?” The key lies in understanding that your people are more resilient than they realize. Teams that have navigated decades of industry shifts have already proven their ability to adapt — even if they don’t recognize it.

The secret is combining this existing resilience with fresh perspectives. You need people who respect the legacy of what’s been built but aren’t bound by it. These change agents bring new tools and approaches while acknowledging the wisdom embedded in your current operations. When you blend these perspectives effectively, transformation feels less like a threat and more like an opportunity.

When we initiated a controlled crisis by moving engineering talent away from a legacy product and toward an emerging platform, the discomfort was palpable. Teams accustomed to legacy workflows scrambled, improvised and ultimately found fresh approaches. Some of our best product innovations emerged not during peaceful times, but during these carefully orchestrated “quakes.”

Related: 5 Urgent Moves to Make to Shield Your Business from the Next Big Crisis

From theory to practice: Leading through transformation

When I took over a century-old industrial division, I inherited an organization that wanted to win and return to relevance. The business was mired in complexity — multiple product lines, various distribution channels and a spectrum spanning from complex engineered solutions to standard retail products. Multiple leadership teams had tried to address these issues, each struggling with the division’s labyrinthine structure.

A failed systems implementation brought the situation to a head. Despite this, the organization remained trapped in old patterns, somehow expecting different results.

In my first leadership meeting, I faced a room full of tired, but deeply committed executives reviewing yet another challenging quarterly forecast. I stopped the presentation mid-slide. “We’re not going to talk about this quarter’s outlook,” I said. “Instead, let’s talk about what we truly want to become.” An HR leader’s candid response — “We just want to be relevant again” — became our rallying cry.

We used that moment to spark a complete transformation — restructuring our go-to-market strategy, realigning our product portfolio and rebuilding customer relationships from the ground up. Within 18 months, we had doubled profits. More importantly, we proved that transformation becomes inevitable when you empower people to make the changes they already know are needed and hold them accountable for results.

Related: Planning to Undergo a Business Transformation? Here Are 5 Tips to Help You Get Started

The final thought: Will you lead or follow?

Here’s the stark reality: Industry titans rarely fall because their products fail overnight. They fall because they waited too long to evolve. By the time they react, the market has already chosen a new winner. The choice is stark: either shape the crisis yourself or have it shaped for you.

During Covid-19, I observed delivery trucks passing by my window while my husband described the struggles of logistics companies facing bankruptcy. While many saw chaos, I recognized an opportunity: the chance to transform a traditional printing company’s logistics division into a cutting-edge ecommerce solution. The pandemic had accelerated the adoption of online shopping by years — making it the perfect moment to reimagine an industry built for the future.

The same opportunity exists for you. Step back and think about your business model. Map out all the ways it could be destroyed — by competitors, technology or changing customer expectations. Yes, it’s terrifying. But it’s also the first step to turning vulnerabilities into opportunities. Reflecting on my decision to dismantle a functional product line, I see parallels to those who thrived by making bold moves early. While many organizations delayed action, the real advantage lay in embracing disruption proactively rather than reacting passively.

The leaders who thrive aren’t the ones best at responding to change — they’re the ones who create it. Will you wait for the next crisis to force your hand, or will you lead the charge?

A new Bank of America study from earlier this month noted that technology like AI could displace up to two billion jobs by 2030. Now Nvidia CEO Jensen Huang says that there’s one thing he recommends everyone do: Get themselves an AI tutor, or an AI chatbot like ChatGPT that can teach them new material on the spot.

“I have [an AI] personal tutor with me all the time,” Huang told journalist Cleo Abram last month on an episode of the YouTube interview show “Huge Conversations.“

“That AI tutor can just teach you things, anything you like, help you program, help you write, help you analyze, help you think, help you reason,” he said.

In September, Huang stated in an interview with Salesforce’s Marc Benioff that he uses the $20 per month paid version of ChatGPT as his own personal tutor to break problems down and learn more about complex topics. ChatGPT also has a free tier.

Related: ChatGPT Can Now Complete a Major Task That Would Take a Human Up to 30 Days. Here’s How it Works.

Huang additionally disclosed in October in an interview with the Bipartisan Policy Center that he also uses Perplexity’s AI search engine daily to learn more about subjects like biology. Perplexity costs $20 per month for the professional plan, but users can access the standard plan for free.

While Perplexity and ChatGPT are designed for tasks other than tutoring, like in-depth research, other AI platforms are specifically designed to act as personal tutors. Khan Academy’s $4 per month Khanmigo chatbot, for example, is advertised as an always-on tutor.

“I feel more empowered today, more confident to learn something today,” Huang told Abram about AI. “The knowledge of almost any particular field, the barriers to that understanding have been reduced.”

^{Nvidia CEO Jensen Huang. Photo by PATRICK T. FALLON/AFP via Getty Images}

Huang also told Abram that if he were a student today, he would focus on learning how to interact with AI like Grok, ChatGPT, and Gemini by being able to ask the right prompts.

“You can’t just randomly ask [AI] a bunch of questions,” Huang said. “Asking AI to be an assistant to you requires some expertise and artistry in how to prompt it.”

Related: Nvidia CEO Jensen Huang’s Biggest Worry Shows that Success Has a Downside

While AI tools can be useful to learn more about different subjects, they still have a high error rate. According to one independent evaluation from Lars Christian Wiik, a senior software engineer at the AI startup Kindly, OpenAI’s GPT-4o had two errors for every 200 responses while Google’s Gemini 1.0 Pro had 12 mistakes for every 200 responses.

AI could also automate work that takes up more than half of the workday today, according to a 2023 study by consulting firm McKinsey, leading to potential job loss. Goldman Sachs predicted in 2023 that 300 million jobs would be lost or downgraded because of AI.

Nvidia is the second largest company in the world at the time of writing, second only to Apple, with a market cap of over $3.2 trillion.

What does it take to start and grow a business to $1 million? Or even $1 billion?

If you’re among the more than six in 10 (62%) of U.S. adults who want to be their own boss, you might be familiar with the basics of entrepreneurship. Still, the prospect of leaving a secure 9-5 job to go all-in on a side hustle or business can be daunting.

Hearing from founders who have already traveled the path to business success — and learning from their mistakes made and wins achieved along the way — can help prepare you for your own entrepreneurial journey.

Related: I Wish I Received This Advice as a Young Entrepreneur

Over the past four years, I’ve interviewed more than 100 successful entrepreneurs who started businesses worth $1 million to $1 billion or more.

I’ve sat down with business luminaries like Richard Branson (Virgin Group), Martha Stewart (Martha Stewart Living Omnimedia), Alexis Ohanian (Reddit), John Mackey (Whole Foods Market) and Bobbi Brown (Bobbi Brown Cosmetics, Jones Road Beauty), among so many others.

No matter how well-known the founders or their particular industries, they, like all entrepreneurs, had to push through business ups and downs to reach success on the other side.

Related: 7 Critical Pieces of Business Advice for Entrepreneurs Just Getting Started

Needless to say, their entrepreneurial careers have taught them a lot, and even if you take just one lesson from their experiences, you could be one step closer to achieving your own business goals.

Read on to see some of their best advice.

Be curious and open-minded

Martha Stewart – Martha Stewart Living Omnimedia

Stewart stresses the value of curiosity — and explains how she uses it to expand her horizons every day.

“Curiosity is certainly a character trait that I think is very important if you’re trying to understand, ‘Where is the world going? What the hell are we doing here? What are we going to do?'” Stewart says. “So I’ve always been happy to be curious. I read a lot. I travel a lot. And one of the things I try very hard to do is never drive down the same street twice if there’s an alternative so that I might see something that I’ve never seen before. And when I travel, I try to do the same thing. I try to see as much as I can in a day.”

Melissa Ben-Ishay – Baked By Melissa

Ben-Ishay isn’t afraid to admit when she doesn’t have all the answers.

“I love to be wrong,” Ben-Ishay says. “I don’t think I know everything. In fact, the older I get and the more experience I have under my belt, the less I know. And that is something I know with certainty. And I think that is an incredibly important mindset for a leader and an entrepreneur.”

Related: 3 Ways to Foster a Culture of Curiosity (and Why You Should)

Arsha Jones – Capital City Mambo Sauce

Jones didn’t grow up in a family of entrepreneurs and says she was on her own when it came to figuring out how to grow her small, home-based business. Without outside money to fund her venture or an extensive network to tap into, she took a grassroots approach instead.

Jones scanned grocery shelves for small bottled brands, “like a local barbecue sauce,” and then sent their owners an email: “I would say, ‘How did you do X? And how did you get on the store shelf?'” Jones explains. “And they would just sit down and answer any kind of questions that I had. And that was really how I jumped over a few of those hurdles, at least in the beginning.”

^{Image Credit: Courtesy of Capital City Mambo Sauce. Arsha Jones.}

Get clear on what you want and stay true to it

John Mackey – Whole Foods Market, Love.Life

Mackey suggests entrepreneurs first figure out if they want to be startup serial entrepreneurs or builder entrepreneurs. “If you’re the serial entrepreneur, then my advice is figure out when is a good time to sell so you can go on to your next thing,” he says.

Mackey’s advice for builder entrepreneurs concerns the critical issue of venture capital. He says most venture capitalists and those in private equity will automatically assume you’re a serial entrepreneur, and “they’ll be looking to replace you.”

“If you are going to be a builder, you should be very clear with the investors that you bring in that you’re not looking to sell the business: You’re looking to build it — you hope to grow it for many years, and the exit for them will not be a sale. It’ll be an IPO,” Mackey says.

Tom Baker – Mr Black Cold Brew Coffee Liqueur

Baker says it’s important to consider your business’s unique offering, even if it slows you down temporarily.

“[I wish we’d] spent a little more time upfront thinking about how we were actually going to recruit drinkers into our brand,” Baker explains. “What will we be better at than every other liquor company? How am I going to get into [customers’] repertoire? I think we probably could have saved millions of dollars and a few years had I just spent another three months thinking about that before we started Mr Black.”

Related: How to Turn Vision Into Reality — A Step-by-Step Approach to Achieving Your Goals

Jackie Summers – Sorel Liqueur

Summers recommends taking breaks to get an accurate accounting of your goals.

“Our culture says you must keep going at 100 miles an hour at all times,” Summers says. “If you don’t have a chance to reflect, you don’t get the opportunity to see what your strengths and weaknesses are and how you’re going to compensate for both. It’s important to cocoon on a regular basis — whether [that’s] 20 minutes of meditation a day or being able to get away once every few weeks and spend some time in nature and quiet your mind. Once you have clarity, all sorts of things can move forward.”

Irene Chen and Matthew Grenby – Parker Thatch

Parker Thatch makes handbags, but its “true mission” is about giving customers a confidence boost, Chen says — a guiding principle that helps other aspects of the business fall into place.

Finding that “why” helped supercharge the company and serves as a solid defense against inevitable industry challenges, like competitors that produce knock-offs, Grenby says.

“That ‘why’ is not something that’s not easily copyable,” he explains. “If it’s not authentic, people sense that, and they value authenticity.”

^{Image Credit: Courtesy of Parker Thatch. Matthew Grenby and Irene Chen.}

Don’t wait forever to start — do take calculated risks

Jenny Just – PEAK6 Investments, Poker Power

Just emphasizes that strategic early risk-taking can pay off in spades.

“When we talk about women taking risks, it’s not about taking bigger risks,” Just explains. “It’s just taking more risks sooner, and what poker allows you to do is take those risks in a bite-sized way.”

Johanna Hartzheim – Wildgrain

Hartzheim recommends jumping in and learning as you go.

“Just go for it because it’s something you learn while doing,” Hartzheim says. “It sounds kind of cliche, but as long as you’re motivated and passionate, you can do anything. I knew nothing about tracking, importing, all these things, but it’s not rocket science. You can learn anything or find the right people who do know these things.”

Related: You Have to Take Risks to Succeed. Here Are 4 Risk-Taking Benefits in Entrepreneurship

Kathrin Hamm – Bearaby

Hamm suggests setting a definitive timeline to put your best foot forward.

“Once you believe in a product, just take a chance and give yourself a year,” Hamm says. “It’s much more manageable if you [have] a considerable time frame where it’s like, Okay, in that year, I’m giving everything I have, 100%. Because sometimes we second guess ourselves. After [a few] months or six weeks, we don’t see the success, [and] we start doubting ourselves. You say [I have] one year, and I’m not asking if this is working. Just have tunnel vision for one year, and then reevaluate after those 365 days.”

^{Image Credit: Courtesy of Bearaby. Kathrin Hamm.}

Embrace failure and the learning-filled journey

Payam Zamani – Autoweb, One Planet Group

Zamani notes that entrepreneurial fulfillment doesn’t have to depend on a business’s success.

“The fact is the overwhelming majority of businesses don’t survive,” Zamani says. “So you want to make that journey worth experiencing, and not just seeking an exit, seeking an IPO that may never happen. Then you feel like, ‘Ah, that was a failure.’ But if you’re making that journey something that’s worth living, you will always feel fulfilled whether or not that climax comes about in your business.”

Bobbi Brown – Bobbi Brown Cosmetics, Jones Road Beauty

Brown suggests giving entrepreneurship a shot so you don’t have to wonder “what if.”

“If you don’t try, you’ll never know,” Brown says. “I don’t believe in failure because it’s just a message that if something didn’t work out, do it differently.”

Related: 7 Ways Companies Can Harness Failure to Drive Success

Ellen Bennett – Hedley & Bennett

Bennett cautions against aiming for overnight success because a slow and steady approach brings some of the biggest gains.

“I’m a huge believer in the long game,” Bennett says. “You can start something out of your house with no money and have a viable, profitable business that you are a majority owner of many years later. And that is awesome. There’s nothing wrong with taking longer to build something great. I know our whole lives are oriented towards speed and how quickly things grow and [becoming] a unicorn, but you can be a long-game unicorn, too.”

Missy Tannen – Boll & Branch

Missy Tannen emphasizes that aspiring entrepreneurs don’t have to have it all figured out from the start.

“You don’t have to know everything day one,” she says. “You’re going to learn so much along the way, and I think if we’d realized all the things we didn’t know, we would have never started.”

^{Image Credit: Courtesy of Boll & Branch. Missy and Scott Tannen.}

Keep your priorities in check

Alexis Ohanian – Reddit

Ohanian wants to reframe the question of what it takes to achieve work-life balance.

“I don’t think it’s about work-life balance,” Ohanian explains. “I don’t think anyone can really accomplish that. It’s not about balancing. If you’re chasing balance, you’re implying, like Thanos, [that] you’d be able to create something perfectly balanced. And the reality is work-life [is] never 50/50. You’ll never achieve anywhere close to that — nor should you. There are times in your life where you will need to focus on the career, the work. There are times in your life when you need to focus on life. It’s on a spectrum that’s ever-flowing back and forth.”

Related: 5 Priorities for Young Entrepreneurs

Do good and do well

Wemimo Abbey – Esusu

Abbey stresses that responsible entrepreneurship doesn’t have to be a zero-sum game.

“We need to find ways where we can create a win-win-win construct across the board,” Abbey says. “We really believe in this idea of justice capitalism: We can do good and do well — and it’s by no means mutually exclusive.”

Cason Crane – Explorer Cold Brew

Crane acknowledges that not every customer will support Explorer Cold Brew because of its LGBTQ+ partnerships, but he’s committed to running a business that reflects his values.

“It certainly helps keep me going every day,” Crane says. “There are things that you do as a business owner to position your business for financial success, and then there are the things you do to keep yourself excited to get out of bed every morning. And I think it’s important as a business owner to do both.”

Related: How to Make Giving Back Part of Your Brand’s DNA

Randy Goldberg and David Heath – Bombas

Goldberg and Heath say founders must ensure the mission is “fully integrated into the business.”

“Every team at Bombas is responsible for the mission in either a direct or an indirect way,” Heath says. “And I think having that so intertwined makes our employees feel good about our mission. But it also makes it so that the mission shows up in everything that we do, from customer experience interactions, to the website, to the creative, to the product. It’s so much a part of our DNA that you could never separate the mission. It’s not an afterthought.”

^{Image Credit: Courtesy of Bombas. David Heath and Randy Goldberg.}

Lead with intention and encourage creativity

Chris Kirby – Ithaca Hummus

Kirby explains what it takes to build a company culture that promotes ideation, risk-taking and learning.

“I’ve learned that true leadership is about empathy, clear communication and creating an environment where people feel valued and empowered,” Kirby says. “So I’ve worked hard to build a culture that’s the complete opposite of what I experienced in a lot of those kitchens. I want my team to feel safe to share ideas, take risks and learn from mistakes without fear of being punished.”

Scott Tannen – Boll & Branch

Tannen says that a business leader is only as good as the people with whom they surround themselves.

“I am not the most talented person in this company by miles,” Tannen explains, “and I think that’s a mark of a great company when I can say that.”

Related: What Makes a Good Leader? Here’s What I’ve Learned After 20-Plus Years as a CEO.

Jocelyn Gailliot – Tuckernuck

Gailliot says Tuckernuck leaders strive to learn from their team members, which means listening to them.

“We constantly ask [them] questions,” Gailliot says. “I’ve been in industries before where it’s very much: ‘This is the role you play at these different hierarchical levels.’ And for us, it’s always been: ‘You’re on the team — you have amazing ideas to contribute, and we want to hear them.’ And we really do.”

Richard Branson – Virgin Group

Branson cites Virgin Unite’s The Elders, a group of independent global leaders working for peace and human rights that has included leaders like Nelson Mandela and Jimmy Carter, as an example of strong leadership.

“They’re all great listeners,” Branson explains. “They know what they’re thinking. They don’t need to hear themselves saying it out loud, and the only way they can learn is by listening to other people talk.”

Work hard to achieve the results you want

Amir Loloi – Loloi Rugs

Loloi says that the only person standing in the way of your business success is yourself.

“If you dream big and work hard, no one is there to stop you,” Loloi explains. “It’s not about the color of your skin. It’s not about your background. It’s not about your religion. It’s not about anything except about you personally: What are you willing to do? When you are given a task, how much more are you willing to add to it to deliver so much more? If you want to be someone in life, step out of the boundaries.”

^{Image Credit: Courtesy of Loloi. Amir Loloi and his sons.}

Adriana Carrig – Little Words Project

Carrig suggests a three-pronged strategy to realize your biggest dreams.

“If you want it bad enough that you’re willing to work for it and believe in yourself, and all those things come together in this perfect trifecta, then there’s nothing you can’t achieve,” Carrig says. “So go for it.”

Related: 7 Elements of a Strong Work Ethic

Fawn Weaver – Uncle Nearest Premium Whiskey

According to Weaver, entrepreneurs need to give the business their all — or rethink it altogether.

“If you’re not going to do it with excellence and with consistency, bow out and get a job,” Weaver says. “Period. If you are going to do it with excellence and with consistency over time, don’t let anybody slow you down — no one. Just keep going after it, because the only people that fail doing it with excellence and with consistency are those who give up before they succeed.”

A Northwestern Mutual study showed that the magic number for retirement, or the number that U.S. adults think they will need to save to retire comfortably, leaped to $1.46 million in 2024, up from $951,000 in 2019.

Americans, on average, reported having saved $88,400 for retirement in 2024, per the same study, leaving a $1.37 million gap between goals and reality.

Now, a new analysis from GoBankingRates released earlier this month examined just how far a hypothetical $1 million in retirement savings will stretch in each state when combined with Social Security benefits.

GoBankingRates used data from the U.S. Census American Community Survey, the U.S. Bureau of Labor Statistics Consumer Expenditure Survey, and Missouri’s Economic and Research Information Center to find how long a $1 million retirement nest egg will last given each state’s cost of living.

Related: Where Do You Have the Most Buying Power? In These 4 Cities, Your Paycheck Is Worth More Than It Seems.

The study calculated the cost of living by looking at the prices of necessities like housing, food, transportation, and utilities in each state. The researchers did not include federal and state income taxes in their estimates. The average monthly Social Security retirement check in January was $1,976, per the Social Security Administration.

The states where retirement funds run out the fastest usually have the highest cost of living and the greatest average monthly expenditures.

Hawaii tops the list; $1 million in retirement savings, plus Social Security benefits, would last less than 13 years in the state. One cause could be high housing costs due to restrictive land use regulations that only allow for 4% of the state’s land to be used for residential purposes. The resulting land scarcity means high home prices — the median price of a home in Hawaii is 2.7 times the national average with a median price of $850,000.

California and Massachusetts are also states where $1 million in retirement savings runs out in less than 20 years. GoBankingRates estimates that monthly expenses in those states are higher than $2,200, with Californians spending more on groceries per month than any other state’s residents. Housing in Massachusetts is priced 108% higher than the national average.

Related: $1 Million Retirement Savings Won’t Last 25 Years Anywhere in the U.S. — But It Will Go the Furthest in These 6 States

On the flip side, a $1 million retirement nest egg could last for over 70 years in five states where the cost of living is low: Oklahoma (71 years), Louisiana (76 years), Arkansas (76 years), Mississippi (87 years) and West Virginia (88 years). Factoring in Social Security, monthly expenses come out to less than $1,200 in these states, per GoBankingRates.

West Virginia has a cost of living 9% lower than the national average, with housing 21% lower than average, according to RentCafe. The World Population Review estimated in a 2024 ranking that Mississippi had the lowest cost of living in the U.S. with the lowest housing prices overall.

Here are the states where $1 million in retirement savings will last the longest, and where it will run out fast.

States Where $1 Million in Retirement Savings Will Run Out More Quickly

1. Hawaii

• Average monthly expenditure cost: $2,761
• Annual total cost of living for one person after Social Security benefits: $80,125
• How many years $1M and Social Security benefits will last: 12.48

2. California

• Average monthly expenditure cost: $2,269
• Annual total cost of living for one person after Social Security benefits: $61,406
• How many years $1M and Social Security benefits will last: 16.29

3. Massachusetts

• Average monthly expenditure cost: $2,340
• Annual total cost of living for one person after Social Security benefits: $51,686
• How many years $1M and Social Security benefits will last: 19.35

4. Washington

• Average monthly expenditure cost: $2,096
• Annual total cost of living for one person after Social Security benefits: $45,629
• How many years $1M and Social Security benefits will last: 21.92

5. New Jersey

• Average monthly expenditure cost: $2,001
• Annual total cost of living for one person after Social Security benefits: $41,315
• How many years $1M and Social Security benefits will last: 24.20

6. Colorado

• Average monthly expenditure cost: $1,899
• Annual total cost of living for one person after Social Security benefits: $39,759
• How many years $1M and Social Security benefits will last: 25.15

7. New Hampshire

• Average monthly expenditure cost: $2,081
• Annual total cost of living for one person after Social Security benefits: $38,052
• How many years $1M and Social Security benefits will last: 26.28

8. Utah

• Average monthly expenditure cost: $1,893
• Annual total cost of living for one person after Social Security benefits: $37,797
• How many years $1M and Social Security benefits will last: 26.46

9. Oregon

• Average monthly expenditure cost: $2,017
• Annual total cost of living for one person after Social Security benefits: $37,346
• How many years $1M and Social Security benefits will last: 26.78

10. Rhode Island

• Average monthly expenditure cost: $2,113
• Annual total cost of living for one person after Social Security benefits: $36,920
• How many years $1M and Social Security benefits will last: 27.09

States Where $1 Million in Retirement Savings Lasts the Longest

1. West Virginia

• Average monthly expenditure cost: $1,833
• Annual total cost of living for one person after Social Security benefits: $11,263
• How many years $1M and Social Security benefits will last: 88.79

2. Mississippi

• Average monthly expenditure cost: $1,784
• Annual total cost of living for one person after Social Security benefits: $11,473
• How many years $1M and Social Security benefits will last: 87.16

3. Arkansas

• Average monthly expenditure cost: $1,725
• Annual total cost of living for one person after Social Security benefits: $13,000
• How many years $1M and Social Security benefits will last: 76.93

4. Louisiana

• Average monthly expenditure cost: $1,785
• Annual total cost of living for one person after Social Security benefits: $13,065
• How many years $1M and Social Security benefits will last: 76.54

5. Oklahoma

• Average monthly expenditure cost: $1,832
• Annual total cost of living for one person after Social Security benefits: $14,048
• How many years $1M and Social Security benefits will last: 71.18

6. Kentucky

• Average monthly expenditure cost: $1,864
• Annual total cost of living for one person after Social Security benefits: $14,456
• How many years $1M and Social Security benefits will last: 69.17

7. Alabama

• Average monthly expenditure cost: $1,794
• Annual total cost of living for one person after Social Security benefits: $14,874
• How many years $1M and Social Security benefits will last: 67.23

8. Iowa

• Average monthly expenditure cost: $1,836
• Annual total cost of living for one person after Social Security benefits: $15,158
• How many years $1M and Social Security benefits will last: 65.97

9. Kansas

• Average monthly expenditure cost: $1,801
• Annual total cost of living for one person after Social Security benefits: $15,315
• How many years $1M and Social Security benefits will last: 65.29

10. Ohio

• Average monthly expenditure cost: $1,853
• Annual total cost of living for one person after Social Security benefits: $16,099
• How many years $1M and Social Security benefits will last: 62.12

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Within startups, especially tech startups, there’s long been this idea that if you’re not growing fast, you’re falling behind. Growth has always meant hiring more people as quickly as possible. But today, I see things a bit differently. Scaling a company doesn’t have to mean adding more people to the payroll. A small, tight-knit team can accomplish just as much, if not more, than a big one — especially if you’re smart about how you run things.

When I started my most recent company, Bread, we wanted to build something impactful without getting bogged down by the typical growing pains that come with rapid hiring. The big question we kept asking ourselves was: How do we make the most out of a small team?

What we found is that staying lean can actually be a huge advantage.

Related: Small Team, Big Success — 3 Ways to Make the Most Out of a Small Team

Why bigger isn’t always better

A lot of startups get caught up in the idea that more people equals more success. But I’ve seen firsthand how quickly that can backfire. The more people you have, the harder it becomes to communicate effectively, and making decisions starts to slow down. Before you know it, you have layers of management and it’s much harder to keep everyone on the same page.

In my experience, keeping the team small has allowed us to stay focused. We can make decisions faster, change direction when we need to and stay close to the work that really matters. We’re not trying to build a massive organization — we’re trying to build something that works well and does what it’s supposed to do.

The perks of keeping it small

There are a lot of upsides to sticking with a small team:

• Quick on your feet: With fewer people involved, you can pivot quickly if something isn’t working or if a new opportunity pops up. If you run your company in short cycles — about six weeks — you’re always in a position to make adjustments without getting stuck in the weeds.
• Communication flows easily: Without a ton of management layers, it’s easier to make sure everyone knows what’s going on. When your team is all on the same page, it makes everything you do more effective.
• Creativity thrives: When you’re part of a small team, you often end up wearing multiple hats, which can lead to some pretty creative solutions. Focus on hiring people who are comfortable switching between tasks — whether it’s coding, designing or strategic thinking.
• Less overhead: Automate your routine tasks so you can focus on the stuff that really matters, and so you don’t need a big admin team to keep the wheels turning.

It might seem counterintuitive but ultimately, having fewer people can allow you to accomplish more.

Related: How Small Teams Can Achieve Big Results

How to make a big impact with a small team

So, how do you scale a company without blowing up your headcount? One of the key strategies my team has employed is automation. By building our own tools to handle tasks like reporting and forecasting, we’ve significantly reduced the time spent on administrative work, allowing us to focus on the bigger picture.

The adoption of low-code and no-code platforms is also becoming increasingly popular. Coding automation tools like these allow small teams to build and deploy applications incredibly fast without needing to hire more engineers.

Making a big impact with a small team requires versatility in hiring. When I’m in hiring mode, I don’t just look for people who are good at one thing; I seek out individuals who can think strategically but aren’t afraid to roll up their sleeves and dive into the work. It’s important to have team members who are comfortable with both the big-picture thinking and the nitty-gritty details.

My co-founders and I have also learned to be selective about the projects we take on. With a small team, it’s impossible to do everything, so we focus on initiatives that align with our strengths and goals.

Small teams, big results

There are plenty of examples out there of small teams doing big things. WhatsApp, for instance, had only 55 employees when Facebook bought it for $19 billion. Or take Basecamp, which has kept its team at around 60 people while serving millions of users. You don’t need a massive workforce to make a huge impact.

For me, the small-team approach isn’t about staying small for the sake of it. It’s about staying lean and focused, so we can do our best work without getting bogged down in unnecessary complexity. I’ve found that when you have a small, dedicated team that works well together, you can accomplish a lot more than you might think.

Related: 5 Ways Lean Teams Can Work Smarter and Get More Done

The small team trend

After the rapid hiring and subsequent workforce reductions that many tech companies experienced in the last four years, I think more leaders are realizing that you don’t need a big team to succeed. It’s not about how many people you have; it’s about how effective those people are. And in a lot of cases, keeping it small might be the smartest way to grow.

As an early entrepreneur, don’t get too caught up in the idea that growth means hiring more people. Focus on building a team that works well together, stays flexible, and gets things done. In the end, it’s not about the size of your team — it’s about what that team can achieve.