39: Started from the Bottom: Tristan Walker's Contrarian Silicon Valley Story

Tristan Walker, former head of business development at Foursquare, is founder and CEO at Walker & Company Brands.

Tristan Walker, former head of business development at Foursquare, is founder and CEO at Walker & Company Brands.

Tristan Walker is the founder and CEO of Walker and Company Brands. He's 33 years old. In this episode I somewhat jokingly say that growing up, he was an odd kid, because of the surface contradictions:

He's a business mind who made a name for himself when he joined a mobile technology startup, but his first company focuses on skin and hair care. He grew up in a working-class family in New York, and his father was killed when he was young – but he went to a boarding school.  

His most prominent investors? Andreessen Horowitz, the marquee Silicon Valley venture capital firm – but he and I speak plainly about Silicon Valley's diversity challenges.  

I recently visited Tristan Walker at the offices of Walker & Company Brands in Palo Alto, CA, the heart of Silicon Valley. This episode was special for me, because, let's be frank: There aren't many African-American technology journalists in this business. I'm one. There aren't many African-American entrepreneurs in Silicon Valley, and Tristan is arguably the best-known. I'm seven years older than Tristan, but we're of a similar generation. We've been a part of this era of sweeping change, and seen what's missing ... and who's missing. 

38: The Brooklyn Kid Turned Angel: Jason Calacanis, Investor


Jason Calacanis's dad had a neighborhood bar, his mom was a nurse. He grew up middle class in Brooklyn in the 70s and 80s.  

Today, he says, his net worth is somewhere north of 100 million dollars. That's not because he's an entrepreneur, though he has started a handful of companies. Jason got RICH as an entrepreneur. But he got really, really rich by investing in the crazy ideas … of other entrepreneurs.  

He just wrote a book: Angel: How to Invest in Technology Startups. He says he can tell you how he did it, and give you pointers so that – maybe you can do it, too. 

In the tech world, we call these people "angel investors." They're usually the first money into a startup, giving six figures or less – just enough to keep an idea going while the founder figures out whether it's big enough to attract millions from venture capitalists.  

The downside of being an angel investor: It's really risky. You're probably going to lose the money you put into 90% of startups. The upside: If you get a couple of winners, they can be huge wins.  

And get this: because of the way regulations are changing, you can now become an angel investor, from the comfort of your computer. You can pool your money with other angels. 

Jason Calacanis is a frequent guest on my TV show, Squawk Alley, on CNBC. He came to the Nasdaq Marketsite in Times Square on a summer day to talk about angel investing – and his life as an entrepreneur.

35: Legacy of the Lemonade Stand: The Skimm's Founders Talk Creativity, Work Ethic and Sexism

Danielle Weisberg and Carly Zakin met in college, and later decided to build their own media brand.

Danielle Weisberg and Carly Zakin met in college, and later decided to build their own media brand.

Danielle Weisberg and Carly Zakin, co-founders and co-CEOs of The Skimm, made a gutsy gamble five years ago. They bet that one of the big problems with the news business was the tone. Media outfits took themselves too seriously, and weren't speaking to young people.  

The pair's solution? The Daily Skimm, a newsletter targeting millennial women that keeps you up to date on what's happening in the world.  

They didn't invent the daily newsletter by a long shot – but Weisberg and Zakin are working the kind of magic with it that should make every media executive in the world sit up and take notice. Here's a little context: The New York Times announced recently that it has 13 million subscriptions to its 50 newsletters. Weisberg and Zakin have 5 million subscribers who open their one newsletter multiple times per week.  

I caught up with Carly and Danielle at The Skimm's headquarters on 23rd Street in Manhattan for the Fortt Knox Podcast. We talked about their journey as business partners and friends, the roots of their entrepreneurial drive, and today's unique challenges for women in the startup game. 

It Began With Lemonade 

Both Weisberg and Zakin had lemonade stands when they were little girls, though one made a lot more money than the other. 

"I would set up a lemonade stand at the intersection of where all the tourists were, and would sell lemonade for way too much," Weisberg says. "I think as young women, our moms always told us, 'You have to have your own way of making money.'" 

Both women had family members who ran businesses, with varying levels of success. They knew it would be hard, but were confident they should give their idea a chance.

They're Thinking Big 

It's one thing to have a single hit product; it's another to build a thriving business around it. Zakin and Weisberg are clearly plotting moves far beyond their popular newsletter. They've also launched an app, which syncs important (and fun) events onto a subscriber's calendar. Overall, they're looking to build a lifestyle brand that accomplishes what morning TV did in its heyday.

"What worked, when you deconstruct it is, it was two to three hours of telling you, here's everything you need to know to be a functioning person: This is the news, the latest movie that's out, the book to read, how to cook your Thanksgiving turkey," Zakin says. "Our audience is not watching morning TV in those ways anymore."

Here's the nugget for entrepreneurs: The founders were TV producers before they started the company, and they've found ways to repurpose those skills for an under-served audience.

Forget Sugar And Spice 

The founders have faced their share of doubters in the five years since they launched The Skimm – and some sexism, too.

"We've had people tell us we're being emotional. You don't say that to male founders," Zakin says.

Weisberg says one potential investor's pitch was, "I'd like to buy some [equity] from you, and it will help you pay for your wedding."

They're not hung up on the roadblocks, they're pragmatic about them. And that might just be part of what helps The Skimm connect with its audience.

34: Nearly booted from high school, Talend's Mike Tuchen learned a lesson he uses as a CEO

Talend CEO Mike Tuchen used learned the hard way that sometimes, you have to double down on your strengths.

Talend CEO Mike Tuchen used learned the hard way that sometimes, you have to double down on your strengths.

By Deborah Findling with Jon Fortt

Mike Tuchen is best when he’s feeling down. Halfway through a project he kicks his efforts into overdrive just when others might start to relax.  

Tuchen is the CEO of Talend, a company with a billion-dollar market value. It helps its customers take advantage of their data and apply it effectively. But before kicking off a career that has included an executive stint at Microsoft and a turn as CEO of Rapid7, he was nearly kicked out of boarding school and had to figure out how to make a contribution as the runt of his Brown University rowing team. 

Tuchen joined the Fortt Knox podcast to share a story that's not your typical wunderkind-makes-good tale. But he shows that when the pressure is on, winning can mean making surprising choices. 

Own Your Choices 

High school was a time of self-discovery for Tuchen, who had just signed up for an elite boarding school filled with talented students. At his old school he was the class brain. With so much competition at this new school, he soon became more of the life of the party.  

When he got shipped home on a three-day suspension, his parents didn't yell at him. They challenged him. Decide what you want to do: Go back and get serious, or quit the school. 

“I realized what I was doing right there clearly didn’t lead me to anywhere I wanted to go," Tuchen says. "I was this close to being not the successful guy I wanted to be – but a high school drop-out.”  

He went back to school, he reset his goals and focused on physics. “I ended up winning the physics prize and in my last few years of school truly winning some awards, being one of the top kids for that.”  

Strategy is Strength 

If you were to sketch an idea of what a Brown University rower might look like it would not be a teenaged Mike Tuchen. Yet, despite standing 5’11’’ and weighing just 155 lbs at the time, he was a key player in their races. 

Tuchen takes lessons from his time on this team to this day. Sitting in the rear, he was responsible for steering the team, building a strategy. 

“You can go for very short bursts of maybe 30 seconds or a minute” rowing your hardest, Tuchen says. “The question is when and how do you use those bursts?”  

Eventually the team started winning races by choosing their moment. At the halfway mark, the team would give it their best push. They could often push to the front, gaining a boat length or more, demoralizing other teams in the process.. 

Tuchen applied these skills to his first management opportunity, using the chance to creating belief and excitement, motivating people around a goal. 

Risk is a Privilege 

Tuchen’s father immigrated to America from Germany, with just a few dollars in his pocket. His scholarship held some constraints but ultimately led him to a job at AT&T – a company where he spent his entire career. 

"That completely changed his life, and created the opportuinity that I had," Tuchen says. 

Where his father could not afford to take many risks, Tuchen took plenty, knowing he had a stable family to support him. Now he appreciates what his father sacrificed so that he could have more options.

31: Playing the Long Game: Steve Ballmer Talks New Beginnings

Former CEO Steve Ballmer is the largest individual holder of Microsoft stock, because he hasn't sold much.

Former CEO Steve Ballmer is the largest individual holder of Microsoft stock, because he hasn't sold much.

Steve Ballmer retired from the Microsoft CEO job three and a half years ago. Then he bought the L.A. Clippers, the basketball team, for two billion dollars.

Ballmer has that kind of money because he's the one person in the world who owns the most shares of Microsoft stock. What's that? You thought Bill Gates owned the most? He did. But he's been selling a lot of it over the years.  

Not Steve Ballmer. He's sold a little, but he's held onto most of it. More than 300 million shares, to be precise. So let's do a little arithmetic. That's 300 million, times 71 bucks a share, which is about where Microsoft was trading at the beginning of June 2017. That's $21.3 billion dollars. 

I had the pleasure of covering Microsoft, and Ballmer, for a good stretch during the past two decades. I got some time with him recently in Rancho Palos Verdes California, at the Code Conference. We put a little of it on CNBC, but I decided to share the whole thing for this episode of the Fortt Knox Podcast. Here are just a couple of highlights:

Wall Street Doesn't Know Everything

According to conventional wisdom, Steve Ballmer's tenure as Microsoft CEO was fraught. The stock didn't do well. Google's search empire emerged and Microsoft couldn't catch up. Apple beat Microsoft in mobile. Ballmer tried unsuccessfully to buy Yahoo (a deal investors were glad didn't happen) and successfully bought Nokia (a deal investors wish hadn't happened).

But here's what the historians often leave out: Ballmer took over just before the dot-com crash, a no-win situation. Despite Google's brilliance, it failed to take down Microsoft Office with Google Docs. Chairman Bill Gates was still working full-time at the company as it missed the modern smartphone and produced the Zune. (If you've been following my writing on LinkedIn, you'll note that I've held this opinion of the Ballmer legacy for a long time: See "Ode to Clippers Owner Steve Ballmer, Underrated Billionaire.")

And ... this is controversial, but I'm just going to put it out there – Microsoft wasn't in such terrible shape when Steve Ballmer retired. When companies are in bad shape, new CEOs clear out senior executives and bring in new blood. New CEO Satya Nadella didn't do that. He has reorganized the leadership structure, elevated some people, made some bold acquisitions; the stock has roughly doubled. Here's how Ballmer put it:

"I think we did a good job building profits; over time there's some correlation that's got to exist between profits and stock price, although this market has sort of said we're willing to be very long-term patient with some [company stock prices] that are way out of whack with the current earnings," Ballmer says. "Frankly, I don't think the stock price had any chance to move as long as I was CEO. People were locked into a worldview about how things were, and sort of the change of CEO let people step back and say, OK, let's think about this thing again."

Facts Matter to Democracy

Another project he's spending time on: USAFacts. It's a trove of information about where our federal tax dollars really go – you can find it at USAFacts.org, and play with the numbers yourself.

Ballmer started digging after his wife asked him to get more involved in the family foundation's charitable work. Ballmer is passionate about making sure kids have the opportunity to do better than their parents did financially. I asked him if there's a philosophical grounding to the idea.

"I won't remember the quote – somebody gave me a Jeffersonian quote on this topic – something to the effect that if you want to have a representative democracy, you have to have an educated citizenry. And I think numbers are an important part of the education process," Ballmer says. "When push comes to shove, you're either writing a law, or you're deciding how much money to put into something. Or you're imposing regulation. Those are the real, three tools of government."

30: Tom vs. the Elephant: How One Billionaire Entrepreneur Keeps Going

Tom Siebel is an entrepreneur, philanthropist, and survivor of a run-in with a five-ton elephant.

Tom Siebel is an entrepreneur, philanthropist, and survivor of a run-in with a five-ton elephant.

To say Tom Siebel has had an interesting life would be putting it mildly. He’s a billionaire, a tech visionary, and the survivor of an elephant goring eight years ago that, by the odds, should have killed him.  

Several doctors told Siebel he would never walk again, much less sail competitively. But he does. 

So what do you learn about life when you’ve stared down death in the form of a five-ton elephant, been crushed by that elephant, and lived to tell the tale? What do you learn when you’ve invented one of the first killer workplace apps of the PC era, then sold it for about $6 billion dollars? 

After you’ve made all that, survived all that, why, at 64 years old, are you still inventing? 

Tom Siebel, now the CEO of C3 IoT, sat down with me for the at the Nasdaq Marketsite in Times Square to share some insight into what’s made him tick – and what’s helped him succeed. Here are some bits to chew on:

Never Say Die 

Tom Siebel had been on a walking safari with his wife and daughters when an elephant attacked him; he says that during his recovery he had 19 reconstructive surgeries and relied on an electric wheelchair to get around. One of his legs was almost completely shattered. Throughout the process, he kept looking for a doctor who could help him to make real progress. 

"I would go visit physicians, and they would explain that they're going to have to remove my leg, and I'd say OK, you're fired." Finally he called the maker of the device that was holding his leg together, and asked what doctor in the world had the most experience installing it. It turned out, the two best were just up the road in San Francisco.  

A few years later, Siebel made a full recovery.  

The lesson here is not so much in what to do if you're trampled by an elephant. (That's probably not going to happen to most of us.) It's in what to do if someone tells you that your goal is impossible: If that goal is important enough, don't just get a second opinion, get expert insight. 

Work for Someone and Learn 

Where did Tom Siebel learn to run a business? From working at Oracle. Where did the leaders at Oracle learn? Trial and error. I asked whether he thinks that's ideal. Actually, no, he says.  

“I think it might be a good idea to go work for another company first and learn about sales, learn about marketing, learn about accounting, learn about compliance, learn about human capital practices," Siebel says. "Maybe learn a little patience, get a little humility.” 

We tend to focus on the exceptions to the rules, people like Steve Jobs, Bill Gates and Mark Zuckerberg. But many of the rest of us would be wise to spend a bit more time learning about business before trying to run one. 

Your Spark Doesn’t Need Approval 

After working for Oracle from its early days until it reached about $1 billion in sales, Siebel had an idea: Rather than just focus on databases, he wanted to build an application – a program that would help businesses keep track of their best sales prospects and close deals faster. He took the concept to Oracle CEO Larry Ellison, who said no. Was Siebel crushed? Discouraged? 

“I was satisfied that it was a good idea, I was satisfied that there was a market there. It was just not a market that Larry Ellison was interested in pursuing at that time," Siebel says. "And I mean, Larry is a very, very bright guy. His successes speak for themselves. But he didn’t have an interest. He didn’t see the market. I did. And I just decided to go for it.” 

Go for it, he did. Siebel Systems became a force in enterprise software, so much that Ellison tried to build his own version to beat it. Ellison eventually decided to buy Siebel out for $5.8 billion instead, with Tom Siebel's blessing. 

No matter how smart your friends – or bosses – are, they can’t make the big career decisions for you. Listen to their advice, and weigh it against what you’ve learned. If you believe you’ve got what it takes, go for it.

28: Married to the Game: Kevin Busque, TaskRabbit co-founder, Guideline CEO

Kevin Busque supported his wife Leah's vision for TaskRabbit, then got out of the way. Now he's launched a startup of his own.

Kevin Busque supported his wife Leah's vision for TaskRabbit, then got out of the way. Now he's launched a startup of his own.

By Deborah Findling, with Jon Fortt

You've probably heard of TaskRabbit – the online service lets you pay a contractor to run an errand, clean an apartment, put together an Ikea bookshelf – any number of odd jobs. Before there was Uber or Airbnb, TaskRabbit birthed the so-called "gig economy." 

You might not know that Kevin Busque co-founded TaskRabbit with his wife, Leah, who he is quick to admit was the brains behind the operation all along.  

In an unusual twist on the typical Silicon Valley story, Kevin and Leah were high school sweethearts, married right after college. They worked at the same company more than once, bootstrapped a business together, and eventually moved across the country to realize the Silicon Valley dream. Leah served as CEO of TaskRabbit for years, and is now executive chairman. Kevin recently launched a new venture, Guideline, a 401(k) platform.  

That unique background as entrepreneur, CEO spouse, and CEO gives Kevin a fresh perspective on how to make big ideas a reality. He shared that with the Fortt Knox podcast. Here are some highlights:

Provide Your Own Path 

Growing up in a military family, Kevin Busque felt the pressure of money being tight. He knew early on if he wanted anything extra, like a car, he had to do it on his own. 

“For me it was really about work ethic; I needed to provide my own path. That's why I started [my first] company – out of necessity,” he says. By building computers with the help of his father and his uncle, he made plenty of extra money. 

Kevin has been working in tech since high school. The first company he worked for, Iris Associates, led to a job at IBM.  

Get Up and Move 


When it came time

for the married couple to move ... the logistics weren't easy, but the decision itself was. 

Before too long, Leah had a startup idea: Run My Errand. When it came time for the married couple to move from Boston to San Francisco, the logistics weren't easy, but the decision itself was. 

“For us, it was never about the outcome, it was always about the journey,” Kevin says. “That was the kicker really. Yeah, let’s go do this. If not now, when?” 

He credits their ambitious nature as part of what drove them to move. Once settled in Silicon Valley, Leah took her first investment from Dave McClure's Facebook Fund. Soon after, she met entrepreneur and investor Tim Ferriss, which led to connections with more investors. This became their funding path, a lifeline for a company trying to find its legs. 

Persistence Counts Double 

As a co-founder and behind-the-scenes player in TaskRabbit's path to growth, Kevin put his full trust in his wife, Leah. Before the company took its first outside investment round, he signed all his stock over to Leah. The vision was hers, anyway. She would be the CEO, and he would support her. 

“I think for us, you just realize that nobody knows your business better than you, even if they have better experience.” he says. “That’s what it takes to be successful in start-up. It’s about hard work.” 

As he supported TaskRabbit's growth as the company's chief technology officer, Kevin realized a lot of the young employees weren't taking the time to sign up for 401(k) retirement plans, perhaps because the process was too complicated. And that's what led him to start Guideline.

27: Solitary Genius Is Not Enough: Citrix CEO Kirill Tatarinov

Kirill Tatarinov got a deep technical education in the former Soviet Union, but realized he needed a new education in teamwork.

Kirill Tatarinov got a deep technical education in the former Soviet Union, but realized he needed a new education in teamwork.

Kirill Tatarinov grew up in the former Soviet Union, the son of a government computer architect. The family didn't swallow state propaganda: His grandfather once spent ten years in a soviet gulag.  

To achieve his dreams, young Kirill would have to get out and move to the other side of the world.  

Tatarinov is now the CEO of Citrix Systems, a tech company with tools that make it easier to share information and get work done from anywhere. His journey to this point – to leading a company with a $13-billion-dollar stock market valuation – includes stops in Israel and Australia, working for startups and for Microsoft.  

It also included a wake-up call about what it really takes to drive a company toward success. 

Genius Is No Substitute for Teamwork

The Soviet educational system focused on deep skills in math and science, but spent practically no time on teamwork.  

"I got my first real management, leadership job in an American company. I saw that I'm lacking the skills, and I saw this gap in my upbringing. And I realized that I urgently needed to fix it," Tatarinov recalls. He was in a company that needed a quick transformation but didn't know how to do it. Tatarinov had been brought on board to speed the process, but he found himself unsure how to bring others along. "After trying it for three or four months, I said, 'I need to learn something new.'"

Part of the answer was an executive MBA program where all the coursework was team projects. Coming out of that experience, Tatarinov found he was able to not only devise a strategy for change, but also communicate it to the team in a way that got them to buy into it and execute.

Marketing Matters

One of the smartest groups Tatarinov had ever worked with was at a networking company in Israel, called Fibronics. 

"It was amazing learning for me. I was a 26-year-old working in that engineering culture. These were all Phd-level programmers," he says. "What Fibronics built back then was without a doubt the best network management system on earth .... They did nothing to market it. As a result, it basically died seven years later."

The underlying message here was similar to what he would later learn about working with people: Quality ideas don't count for much if you can't communicate them. Doing that inside an organization looks like teamwork. Doing it outside looks like marketing. Often success requires both.

Get Broad Knowledge

Tatarinov warns against focusing too much on subject matter expertise to the exclusion of everything else. It's important to have technical skill, of course. But he would advise today's college students to spend years studying subjects like literature and history before diving deep into engineering.

"You really need to have the broad perspective. Because frankly, even if you go deep into one field, the breadth of knowledge and ability to grasp different disciplines and correlate them in your head is very important," Tatarinov says. "It's not just about correlating math with physics – of course, they're inseparable. It's about thinking through history's lessons."

That way you'll know which lines from Shakespeare or Dostoyevsky to quote to rally your team around the new strategy

26: Starting a Business and Keeping it Going: Dell CEO Michael Dell

Since Michael Dell launched his company 33 years ago, he's amassed a personal fortune that Forbes estimates at more than $20 billion.

Since Michael Dell launched his company 33 years ago, he's amassed a personal fortune that Forbes estimates at more than $20 billion.

Michael Dell founded his company 33 years ago, in his freshman dorm room at the University of Texas, Austin. He had $1,000 to buy PC parts, and took orders over the phone. 

After that, it ballooned like crazy – and made Dell Computer one of the fastest-growing companies ever. The stock price went on a dizzying tear throughout the 1990s, roughly doubling most years throughout the decade. It also made Michael Dell a multi-billionaire. 

Since then, the path hasn't been easy. The era of gonzo growth in personal computers and corporate servers – Dell's bread and butter – is over. Now attention has turned to smartphones and cloud computing.  

Sensing weakness, legendary investor Carl Icahn tried to buy out the company four years ago, which probably would have resulted in it breaking into pieces. Michael Dell fought him and won, taking his namesake company private, and then making it bigger than ever. 

I went to Round Rock, Texas to talk to Michael Dell just days before his Dell EMC World conference in Las Vegas. We talked about the product news for CNBC viewers, but we also talked about his journey for the Fortt Knox podcast – about almost losing a company he's spent nearly two thirds of his life building, and how he developed the skills he needed to become a legendary founder-CEO … and survivor. Here are just a few highlights:

Be Unique 

Dell recalls that he had a love for numbers growing up – and that led him to pursue different activities than a lot of his peers in Texas in the late 1970s. 

"I was in seventh grade math class, and we had this thing called Number Sense. So, I wasn't on the track team. Wasn't on the football team. Wasn't on the basketball team. I was in the Number Sense Club," Dell says. "So this math teacher got a Teletype terminal. So you'd write a program, Send it off to the big computer in the sky, and the answer would come back. I was pretty fascinated by that." 

At a time when society is encouraging kids to tackle all sorts of activities to pad their college applications, it's instructive: Sometimes it pays to be different, and focus on the talents and skills that are unique to you. Go deep.

Ideas Aren't Everything 

I asked Dell what he thinks tomorrow's Michael Dell is noodling with in his or her dorm room right now. I mean, he's probably not building PCs. In 1984, personal computers were cutting edge; in the mid-1990s it was websites and web portals. Is it artificial intelligence? Virtual reality? 

His response: It's not the what so much as the why

"You have to do stuff that you're actually incredibly passionate and excited about, and you know something about," Dell says. "The oppor-tuneurs don't do as well as the entrepreneurs." 

In other words, he believes his success was less about him building PCs in 1984, and more about him following his technology obsession. It recalls the advice Twilio CEO Jeff Lawson gave on Fortt Knox: Don't pursue a business venture just because it sounds like a sure-fire moneymaker. 

Study Up 

No matter how successful you are in the beginning, you've got to keep learning. Five years into his Dell Computer adventure, in 1989, Michael Dell flew to California to take business classes at Stanford. While he was there, he decided to put together his own advanced curriculum. 

"I called up a bunch of the CEOs of Silicon Valley companies, and said 'Hey, can I come and see you? And I'd like to learn about what you're doing.' And I don't know, most of them said yes," Dell says. "Irwin Federman, and Jimmy Treybig, and Andy Grove. ... You go see these guys, and you know, 'How do you manage a big company?' and they would talk to me. That was great. I was doing everything I could to learn and get help." 

25: How Alexandra Lebenthal Has Taken On Wall Street's Boys' Club

Alexandra Lebenthal has been connected to Wall Street all her life; her grandparents founded Lebenthal & Co. in 1925.

Alexandra Lebenthal has been connected to Wall Street all her life; her grandparents founded Lebenthal & Co. in 1925.

Alexandra Lebenthal is a third-generation Wall Street power broker. Her grandparents started Lebenthal & Co. 92 years ago, helping to redefine the municipal bond business.

Her company has seen better days — she's in the process of selling much of it to South Street Securities Holdings, though she'll maintain control of the corporate bond operation.

Through the years, Lebenthal has shown a determination to maintain the family business, and to blaze a path in the boys-club world of finance. I sat down with her for the Fortt Knox podcast to talk about growing up in New York's financial world, her view of gender imbalances in the corporate environment, and how she feels now that her college-age daughter has surprised her by deciding to follow in her footsteps.

Here are some of her insights:

Find your gym

Though she grew up watching her grandmother Sayra run the family business, Lebenthal says she realized she still needed confidence boosts. An all-girls school on the Upper East Side of Manhattan, the Nightingale-Bamford School, provided that environment in high school.

Lebenthal particularly remembers headmistress Joan McMenamin: "If she said it once, she said it every single day: 'Girls, you can do anything you set your mind to.' For anyone to hear that over and over, it does drill into you. … You always need to hear it, at every stage of your life. Even as you're a grown-up."

The universal lesson here: Even after we've heard the motivational speeches and seen success up close, we still need a tune-up now and then. Find the places and people that help you shore up your weaknesses and gain confidence in your strengths.

Never hear no

When Lebenthal decided to rebuild her business 10 years ago after selling control, Merrill Lynch, which had acquired the family name, at first refused to sell it back to her. She didn't give up.

"That is one of the things I have learned in life, is, never hear no. Just think of it as a placeholder until you figure out how to get to yes."

How many times did she hear no in that case before she figured it out? "I got four, and one of them was from Stan O'Neal [the CEO at the time]."

She also remembers a time in the 1970s when her father faced a crisis that nearly sank the business. Things worked out in the 11th hour. "As an entrepreneur, you're always going to have moments of great challenges. And the trick is keeping yourself together and getting through them."

Stand out

Lebenthal never has been much of a wallflower, and that's reflected in her fashion choices. Don't expect to see her in a boxy, black power suit.

"Believe it or not, I actually embrace being in a room where I'm the only or one of few women, because I think, 'Hey, here's my opportunity. I don't look like everyone else. I don't dress like everyone else. So let me be in as bright colors and big jewelry as possible, and just figure out, OK, how can I make this ultimately be something beneficial for me in business.'"

It's a lesson in taking the trait that otherwise could be a disadvantage and finding a way to make it work for you.

24: Be Sure the Sleeves Match the Cuffs: Ford CEO Mark Fields

Ford CEO Mark Fields had to compete with two older brothers growing up, which forced him to aim high.

Ford CEO Mark Fields had to compete with two older brothers growing up, which forced him to aim high.

For Ford Motor Company CEO Mark Fields, the love of cars started early; he still remembers the set of Matchbox cars his dad bought him for his 6th birthday.  

Of course, love of cars alone wasn't going to get him to the helm of the second-largest U.S. automaker, and a brand that's been around for more than a century. That would take a mix of competitive spirit, adaptability, and a knack for getting teams to focus quickly. 

Mark Fields leads a company that last year sold more than 6.6 million cars, bringing in more than $141 billion from vehicle sales. In the era of Uber and Tesla that's getting harder by the day. 

I talked to Fields for Fortt Knox about his leadership philosophy, his motivation, and how he made it to the top. Here are a few highlights: 

Run to the Fire 

Fields was CEO of Ford's Mazda subsidiary in his late 30s, a stunningly fast ascent. How had he risen so quickly? He chalks it up to his eagerness to find tough problems and volunteer to solve them.  

"I've always had the philosophy, always run to the fire," he says. "Run to those really challenging situations or businesses that you can learn a lot, but also contribute a lot." 

Pull this off this a few times, and you're likely to get a reputation for making the bosses look good. When you've done that on high-profile projects, that's often a ticket to a promotion.  

Punch Above Your Weight 

I was curious about Fields's motivation. How had he developed his drive to succeed? 

"I'm the youngest of three boys," Fields says. "So listen, if you weren't fast at the kitchen table, or in sports, because you know, you get knocked around – that was part of it." 

Birth order isn't destiny. But for someone looking to fuel his ambition, it's one of many things he could draw on.  

Be Sure the Sleeves Match the Cuffs 

Several times in his career, Fields needed to quickly get a new team working toward a common goal. He has an interesting method for getting people to trust him when they barely know him: He'll take a half day and do a session on who he is and what he values. 

"So from the get-go, people can say, 'Oh, OK, I kind of get the gist of this guy. And so once you get that out of the way, then you can get on with the work. And then importantly, I have to live up to what I talked about in terms of my leadership. Because if the sleeves don't match the cuffs, people just think you're trying to manipulate them." 

It's a tailoring metaphor that works: If the sleeves don't match the cuffs, you've getting ripped off. Effective long-term leadership has to be authentic, too. 

23: He's Not in Kansas Anymore: How FCC Chairman Ajit Pai's Roots Will Influence Internet Policy

Ajit Pai is the new chairman of the Federal Communications Commission, elevated by President Trump. 

Ajit Pai is the new chairman of the Federal Communications Commission, elevated by President Trump. 

Ajit Pai doesn't come across as the sort of guy who'd be crossing swords with Silicon Valley. 

Question him about controversial topics and his answers come quickly, but always tempered by a Midwestern sincerity. Among the current crop of communication industry regulators, he was the first on Twitter. 

But yes, Pai is a controversial figure in the tech world. President Trump appointed him chairman of the regulatory body, and one of his first moves was to roll back regulations that would have prevented broadband providers from using your Internet browsing history to sell you advertising. I asked him about that – and more – for Fortt Knox. 

Here's some of what he told me: 

It Goes Back to Kansas 

Pai is the son of two doctors, and recalls growing up in rural Kansas, where his dad sometimes would have to drive more than an hour to see patients. He says that aspect of his background – being disconnected from big-city and suburban conveniences – influences the way he looks at his role shaping policy. 

"It's the fundamental driver of the policies that I'm trying to promote at the FCC, because I've seen for myself in my own childhood and as a commissioner having traveled around the country from Alaska to Mississippi, that there are some big gaps in America in terms of connectivity," he says.  

The first policy priority he lists on his FCC bio is the expansion of broadband, including to rural areas. That might even help doctors to see more patients digitally when they don't specifically need a house call. 

Same Rules for Everyone 

The way many of the headlines about Internet privacy rules are written, Pai's stance on letting Internet service providers market your usage data doesn't make sense. Why would you want to let Comcast (the parent company of CNBC's Fortt Knox) or AT&T, or Verizon, etc. sell that information? Pai argues that's not the point. Companies like Google and Facebook already have access to tons of information on us, Pai argues. Unless we set a level playing field, we let them off the hook. 

"We just want every company that is handling consumers' data to handle it in the same way. I think that's something that would give consumers a much better sense of confidence when they go online," Pai says. 

In other words, if you're outraged about Comcast selling your browsing habits, you should be just as outraged about Silicon Valley doing it. First level the playing field, then make rules that apply to everyone. He has a lot of skeptics to win over, especially in the tech world. 

A Light Touch 

Like many Republican public servants in government, Pai argues for a light touch when it comes to interpreting the law. (You'll see similar language coming out of new Supreme Court Justice Neil Gorsuch.) That sets up an interesting contradiction when it comes to tech issues. 

Silicon Valley loves to smash regulations when it benefits their innovation argument. Look at Uber and Airbnb trying to smash taxi and hotel regulations, for example. When the shoe is on the other foot, though, Silicon Valley leaders tend to love regulations like Net Neutrality, which they argue keeps broadband providers from stifling innovation. 

That's why some in the tech industry are skeptical of Pai, who argues for a light touch in some places where they want a heavier hand. 

"I view my role as being a rather boring, frankly, and humble one," Pai says, "which is to take a look at the papers that are in front of me, and analyze the facts soberly, and make an informed decision based on the law and the precedents." 

In a time when the rules in technology and content are shifting at an unprecedented pace, we'll have to see what that really means.

22: A Founder-CEO's Secret to Success: First Get Started, Then Get Smarter: Twilio's Jeff Lawson

Twilio co-founder and CEO Jeff Lawson learned that you get more done by tackling big problems and doggedly improving as you go.  

Twilio co-founder and CEO Jeff Lawson learned that you get more done by tackling big problems and doggedly improving as you go.


Among the many business lessons Jeff Lawson has learned, there's this: Don't expect to get things done if you wait until you're perfectly prepared. 

Lawson is co-founder and CEO of Twilio, a company that makes it easy for apps to contact you. (Ever wonder how you can send a text to your Uber driver in the app, or get one in OpenTable when your seat is ready? Twilio does that.) 

Twilio went public last summer at the New York Stock Exchange, and is now worth about $2.5 billion. As it pushes to make apps communicate better, the scrappy San Francisco company has developed a culture that favors boldness and taking initiative, and frowns on perfectionism.  

I caught up with Twilio's CEO at a tech conference in Barcelona, Spain to talk about his journey from curious kid in the Detroit suburbs to CEO of a public tech company. Among the things I love about Lawson's story? It's about the setbacks as much as the successes, and learning along the way. 

Here's some of what I gathered: 

Ask for the Keys 

Lawson likes to tell a story about his grandfather, who worked in a factory and needed to earn more money. 

"He went to the owner and he said, 'I need to make more money, how do I do that.' The guy said 'I don’t have any other jobs. The only job I have is driving the truck. Do you know how to drive the truck?' My grandfather's answer was, 'Give me the keys.'" 

What his grandfather didn't mention was that he'd never driven a truck before in his life. But he got the job, figured it out, made more money. 

Chalk it up to genetics or coincidence, but in middle school Lawson started a company shooting video footage of weddings, and he used the proceeds to buy more sophisticated equipment. 

"The best way to learn something new," he says, "is to commit yourself to doing it." 

You've Got to Love It 

There were some false starts. In college during the dotcom boom, Lawson learned software development and started a company that sold for millions of dollars … in stock. He thought he'd made it big, but when the bubble popped, his windfall vanished.  

Later, he got the opportunity to be founding chief technology officer of StubHub, a ticket sales company that would later sell to eBay for $310 million. But Lawson didn't stick around for the payoff.  

"It was a fine business, but I wasn't the customer and I didn't feel passionately that the world needed the product we were building." He wasn't a concert goer, so he didn't feel inspired to keep working on it. "As an entrepreneur, I think you need that." 

Hindsight being what it is, it's easy to fault Lawson for missing his share of a nine-figure payday. But remember, he's got a share of a 10-figure payday in Twilio. 

Knowledge and Reputation 

So how did Lawson do it? How did he rebound from a missed nine-figure payday cleanly enough to do himself one better? First he made another valuable mistake or two, which you’ll learn about listening to the podcast. More important though, he was able to focus on the two most important assets he was building in each of these experiences. 

"The best thing that we have as we go through our careers is our knowledge and our word – our reputation," Lawson says. "If you're constantly building those two things, I think generally speaking, good things end up happening to people."

21: Innovation From Spotting Details and Asking Questions: Logitech CEO Bracken Darrell

Bracken Darrell launched products like deodorant and washing machines before leading one of tech's hidden turnaround stories.

Bracken Darrell launched products like deodorant and washing machines before leading one of tech's hidden turnaround stories.

Not many executives can say they've studied the finer points of everything from deodorant and washing machines, to Bluetooth speakers and gaming keyboards. 

Bracken Darrell can. Darrell is CEO of Logitech, a company that once specialized in mainstream PC mice and keyboards. One of the remarkable things about him is his appetite for learning. His curiosity has led him from a modest upbringing in Western Kentucky, to leading one of the smartphone era's most remarkable turnaround stories. 

I sat down with Darrell for the Fortt Knox podcast to find out how his upbringing shaped him, and how his curiosity helped him find his way to the C-suite. Logitech's stock has quadrupled since he took over four years ago; the company's now worth $5.5 billion. 

Start from the Bottom 

Darrell's parents split up when he was a preteen. He grew up in Owensboro, Ky., one of four siblings raised by a single mother. As a result, he never had to look far for motivation. 

"I had it easy. I didn't have a choice. I had to make it," Darrell says. "We literally would wear the same jeans all the time. Like a lot of people – I'm not a Horatio Alger story, I mean, we had plenty to eat. But we didn't have any money. It didn't make me particularly money-conscious, but I certainly did always envy the opportunities that I thought were available to people who had money that I didn't. It's really ironic, because now that I look back on it, it's the biggest advantage I ever had." 

It's a lesson that applies no matter what your circumstances are in the beginning. If you understand what it means to make do with less, it can help you stay focused and resist a sense of entitlement.  

See the Whole Room 

Darrell turns to literature and the arts to help him think about things in new ways. One book, Thinking, Fast and Slow by Daniel Kahneman, shifted the way he looks at solving problems. A conversation with leading brain researcher Henry Markram helped illustrate just how much information we miss every day. 

"He said when you walk into a room when you're a little, tiny child, you soak in the whole room. You see it all. When you walk into the room as an adult, you see this sliver in the corner, and you build the room in your brain. You actually don't even see it," Darrell says. "That made a big mark on me. Think how many mistakes we make in our roles because our brain's building based on pattern recognition, and we're not seeing or thinking anymore, objectively." 

The rub, here: From a primitive perspective, it makes perfect sense. If you're walking through the savanna, you don't need to notice every blade of grass, but you need to see the lion that wasn't there before. 

But business is different, Darrell says. We need to force ourselves to look at ordinary things in extraordinary ways if we want to win.  

Sniff Out Genius 

Problem-solvers also need to get smart about odd topics in short order. One of the best ways Darrell has found to do that? Find the smartest people in your organization and pick their brains. It might sound obvious, but people are often intimidated by the engineers and scientists who might hold the key to figuring out a business problem. They're not always invited to the meetings where decisions get made. 

Darrell saw the benefits to this up close while working for Procter & Gamble. He was working on the Old Spice deodorant product, trying to reinvent the brand and turn it around. He sat down with a chemist and told him he wanted a simple, visible way to show their product was better and lasted longer. 

"He said, 'We have propylene glycol in this.' And propylene glycol evaporates less fast, and that's one of the reasons why this product is better – not the only reason, but it's one of the reasons why it lasts longer," Darrell says. The result was a commercial for high endurance deodorant that showed a time lapse video of the competitor's product evaporating faster than a swipe of Old Spice. 

"Those were the most boring commercials in the world," Darrell says now, "and I'm responsible for them." (I'm not so sure about the boring part. More than 20 years later, this Gen Xer still remembers them.)

20: She Didn't Take No For An Answer: This Exec Cracked Silicon Valley and D.C.; Color CMO Katie Jacobs Stanton

Katie Jacobs Stanton ran Twitter's international business and launched Google Finance; now she's helping to lead a genetics startup.

Katie Jacobs Stanton ran Twitter's international business and launched Google Finance; now she's helping to lead a genetics startup.

Katie Jacobs Stanton knows how to create her own options. 

Stanton, a veteran of Twitter, Google, Yahoo, and a presidential administration, now serves as chief marketing officer of genetic testing startup Color Genomics. Her professional journey from East Coast to West, and back and forth again, has given her rare insight into the workplace cultures that shape us today. 

I sat down with her for the Fortt Knox podcast to talk about the environment for women in tech, and her journey to the executive ranks in Silicon Valley. Here are some key lessons I pulled from our conversation: 

Outsmart the Culture 

Stanton's timing was great, joining Google in 2003 after a stint at Yahoo and a maternity leave. But she encountered some obstacles right out of the gate. 

"When I was at Yahoo, I was hired as a product manager for Yahoo Finance, and helped build the site and build it internationally. And so when I came to Google, naturally I thought, 'I can be a product manager here.' And Google said 'No, I'm sorry, you don't have a computer science background.' And I was like, but I just helped build this great product on the web, and I've been there for three years, and I was promoted." 

The leadership structure at Google was unmoved. No computer science background, no product management. 

But that didn't stop Stanton. She found some engineers who would work with her, and brought Google Finance to market. Along the way, she gained a reputation as a person who could ship new ideas.  

Move Around 

Stanton is from New York, went to college in Tennessee, ditched the East Coast for Silicon Valley in her 20s, and did a stint as director of citizen participation in the Obama administration and as a technology advisor in the State Department before heading back to California. International travel has helped broaden her horizons; she was serving as vice president of Twitter's international business when the company went public. That now influences what Stanton looks for when she's hiring. 

"I look for people with international experience, something I believe strongly in. People who speak foreign languages, I think, have always stood out to me." Stanton says she looks for those qualities even in roles that don't require it. "I think it just brings a different lens and a different empathy, a different perspective to things." 

As someone who hadn't traveled internationally when I started my career, I couldn't help but notice that in some ways, Stanton's preference for well-traveled people could be as limiting as Google's preference for coders as product managers. The key, it seems, is to show you can deliver what the job requires even if your résumé isn't the obvious fit. 

Find Role Models 

Stanton was fortunate enough to work for a string of female bosses during her six-year run at Google, an experience that's pretty rare in Silicon Valley's tech scene. She says having women in leadership positions will also be important to the next generation. 

"You can't be what you can't see. I think for a lot of girls, not seeing other female professors of computer science, other leaders in business" can be a barrier. "We still have a lot of work to do for women in leadership positions." 

She's certainly doing her part.

19: How To Make Your Second Act An Empire: WPP CEO Sir Martin Sorrell

WPP CEO Martin Sorrell started building his company at age 40, after serving as CFO for Saatchi & Saatchi. He's still going strong at 72.

WPP CEO Martin Sorrell started building his company at age 40, after serving as CFO for Saatchi & Saatchi. He's still going strong at 72.

Sir Martin Sorrell is arguably the most important advertising executive in the world.

As CEO of WPP Group, he oversees a global marketing machine that he's assembled over more than 30 years. His group companies include J Walter Thompson and Ogilvy & Mather, Young & Rubicam, and more than 100 others. Clients include two of every three Fortune Global 500 companies.  

When I sat down with him for the Fortt Knox podcast, I wanted to talk about his childhood, his career, and the pivotal choices he made. He didn't disappoint.  

Here are some of the best lessons: 

It's Never Too Late 

Sorrell was chief financial officer at upstart ad firm Saatchi & Saatchi when he decided to quit and build his own company. He was 40 years old. In an era when Mark Zuckerberg, Evan Spiegel and the Google founders are starting companies in their teens and early 20s, that might sound like a late start, but Sorrell doesn't see it that way.  

"I thought it would be good to have a go. I'd made a little bit of money, and borrowed 250 thousand pounds," he says. "Forty in those days used to be a pretty critical age. Because you think of yourself starting work when you're about 20, you come out of college, and finishing when you're 60. Now, of course, here I am at 72 still going." 

Then again, Sorrell doesn't seem to obey the calendar like most people. Today he's the father of an infant daughter, his fourth child.  

Grow a Thick Skin 

Sorrell's tactics building WPP have not always been genteel. As he aggressively built out his holding company, he sometimes employed hostile takeovers. At the beginning of one such campaign, when he targeted Ogilvy & Mather, founder David Ogilvy famously referred to Sorrell as an "odious little s--t." (In the press, the comment was sanitized to "odious little jerk," and Sorrell seized upon it as a point of pride.) 

Sorrell later won Ogilvy over. I asked him where he learned to shrug off the attacks that have come with the job.  

"It gets into fairly tender stuff. When you're from the northwest London ghetto – I use the ghetto loosely, because it wasn't really a ghetto – Golders Green, Edgware, Mill Hill – you probably develop a pretty thick skin. People say things at school," when you're one of the few Jewish kids, he says. "In those days there was a fair bit of invective, and it's water off a duck's back. What I had to go through was nothing near what my parents had to go through, or my grandparents had to go through." 

No one should have to suffer bigoted put-downs, but a young Martin Sorrell was able to build up a degree of immunity to it. It clearly helped him in business later. 

Hunt Buried Treasure 

When Sorrell targeted ad agency J. Walter Thompson for takeover, one of the things he had his eye on was freehold property – land and buildings that the target owned outright. From his days as a chief financial officer, he had learned that this often could amount to buried treasure. Companies weren't required to re-value such real estate holdings as their value rose. To make a long story short – even though WPP paid a pretty penny for JWT, Sorrell quickly discovered hidden real estate holdings that effectively paid him back a huge portion of the sticker price. 

The universal lesson here for your career makeover? Sometimes finding buried treasure is just a matter of knowing where to look. Fortunately, Sorrell's previous job had armed him with that knowledge.

18: Tom Steyer: A Billionaire's Surprising Rules of Winning

Billionaire investor Tom Steyer talked about his career and his activism when we sat down at the New York Stock Exchange.

Billionaire investor Tom Steyer talked about his career and his activism when we sat down at the New York Stock Exchange.

Tom Steyer became a billionaire by solving puzzles.  

That wasn't his technical job description – he actually founded Farallon Capital, a hedge fund in San Francisco, 30 years ago. As an investor, two signature moves stand out: One, he got his alma mater, Yale, to invest a portion of its endowment with him; the success of that arrangement sparked a trend. Two, he often made his own luck by investing deeply in countries and industries.   

As Steyer scouted unusual investments in unexpected places, he followed some basic rules. Now that Steyer has set his sights on politics and policy – he's rumored to be considering a run for California governor – I sat down with him for Fortt Knox. He gave me some of his best insights on how to succeed, and why he's fighting the new administration in Washington, D.C. 

No Lopsided Deals 

Steyer has a different take on dealmaking than fellow billionaire President Trump does. In his experience, building an investment giant from scratch, it's important not to push your advantage too far. 

"I don't want to take advantage of you. I really don't. Because you're smart. And so if we do something together and I get 80% of the value and you get 20%, why would you ever deal with me again? What I want to do, is do 25 things together where we each go 50-50, and we don't have to fight each other. We each spend all of our time trying to make the whole pie as big as possible, and no time fighting about how to slice it up." 

I point out that Mr. Trump seems to have done just fine treating people the way he does; Steyer's response is thought-provoking. 

Execution Beats Planning 

These days, the culture tells us we're supposed to have a long-term plan for everything. Steyer's experience gives another point of view. Rather than always trying to devise the perfect roadmap for life, which is bound to change anyway, we should focus on getting the most out of the opportunity in front of us. 

"I went to Yale College. Why did I go? Not sure. … I went because I thought it was a good school, and what that meant, I'm not sure I knew. Because it was sort of famous. And so I thought, I'll go to a school that has a reputation for being a great school. And I don’t think it was that much more complicated," Steyer says. "I wished I'd gotten recruited to play sports. And I played sports all through college. I was the captain of the Yale soccer team. But I walked on to the Yale soccer team. And you know, I thought – I love sports. I'm playing sports because this is super, super fun, and I love doing this." 

Strategy is still important. But the biggest wins often come in un-plannable moments. 

Curiosity Rules 

At a certain point – after tens of millions of dollars in earnings, one imagines – Steyer's wife pointed out that he didn't have to keep working. Their family goal, he says, was to sock away enough to have a house, pay for healthcare, and fund retirement. Anything you do from here on out, she said, you should do because you love it. Steyer agreed – and he kept investing. Why? 

"I love puzzles. I love figuring things out. I'm someone who really is interested in how companies work, and how industries work, and figuring out – that's the biggest puzzle in the world! How do you think about a Saab dealership in South Africa," he says. 

Curiosity is a prized attribute in an investor, but it applies to other fields, too. It not only helps to keep the work interesting, but also pushes us beyond what's been done before.