56: Can We Save Young America from Financial Ruin? Justin Dent, co-founder, GenFKD

 
Justin Dent is co-founder and executive director of GenFKD, a non-profit helping millennials avoid getting financially screwed.

Justin Dent is co-founder and executive director of GenFKD, a non-profit helping millennials avoid getting financially screwed.

Justin Dent is the co-founder and executive director of GenFKD, a non-profit dedicated to getting Millennials smarter about their finances before it’s too late. He’s a Millennial himself – he graduated from the University of Maryland just a couple of years ago.  

Dent didn’t come from money, and neither did I – we’re both African Americans, though from different generations, who grew up on the East Coast and had to fight the odds to get into a better financial position.  

With the tax changes that are wending their way through Congress and the questions about who they’ll help or hurt, it’s worth having a bit of an American family meeting. We should think about just how we got into this sorry state, and how we get out. Dent is taking a bold step at a young age, toward doing exactly that.

55: The Father of the Cloud: Amazon Web Services CEO Andy Jassy

 
Andy Jassy joined Amazon straight out of grad school in 1997, the year the company went public. Later he dreamed up AWS.

Andy Jassy joined Amazon straight out of grad school in 1997, the year the company went public. Later he dreamed up AWS.

About 13 years ago, Andy Jassy had a big, big idea. What if you could rent computing power and storage over the Internet instead of having to buy a whole bunch of equipment?  

Jassy worked for Amazon.com at the time, as the technical assistant to one Jeff Bezos – the founder and CEO of Amazon. He told Jeff about the idea. They decided to do it. And now, more than a decade later, Andy Jassy has not only built a business that brings in 16 billion dollars a year. He and his team also essentially invented the business of cloud computing, and upended the tech world in the process. 

I flew out to Las Vegas this week to have a chat with Andy Jassy, the CEO of Amazon Web Services. The company was having its annual re:Invent conference, where software programmers from around the world gather to hear the latest cloud tools Amazon is looking to put in their hands.  

I wanted to hear from him about how he got started at Amazon; how he worked with his boss, Jeff Bezos, to launch a business that has turned out to be Amazon's biggest profit-maker; what his strategy is now, and just how massive he thinks it all can get.

Saying No to Jeff Bezos

Part of the reason Jassy was in a great position to suggest Amazon launch the first large-scale cloud computing business was proximity to Amazon founder and CEO Jeff Bezos. He had been serving as Bezos's technical adviser for about a year when he came up with the idea. Interestingly, he initially turned down Bezos's offer of the role.

"It was a very undefined role," Jassy tells me. "When I talked to Jeff about it, I said, 'Well, what's the goal of the role?' He said, 'Well, the goal is for me to get to know you better, and for you to get to know me better, and to build some trust.' And I thought, Well that's interesting, but it doesn't sound like a mission."

Things came together because Bezos was willing to let Jassy craft the role into something more like a chief of staff to the CEO – and that made a lot more sense to Jassy.

The Wrong Way to Think About Being Right

Jassy says that kind of flexibility is a key to healthy leadership. Too many leaders, he says, misunderstand the real point of being correct.

"They think that being right a lot means that the idea has to come from you," he says, "and you dig in on your idea and you have to win the argument. The job for all of us as leaders is to make the right decisions."

How Big Amazon's Cloud Can Get

Jassy, Bezos and Amazon's senior leadership team certainly were right about the potential of the cloud computing business. But how big can it get? I asked him if he thinks Amazon Web Services could become the biggest enterprise cloud company on the planet.

"I do think it's possible," he says. "It has the chance, I think, to be a really large business. And I think that if we are able to accomplish the right type of customer experience and continue to build what customers ask us over time, as the market moves more and more toward cloud, I think we have the chance to be the largest enterprise company in the world."

We'll have to wait and see if he's right about that.

54: An American Brand In A New Generation: Black Enterprise CEO Earl "Butch" Graves, Jr.

 
Earl "Butch" Graves, Jr., CEO of Black Enterprise, is transforming the media company his father founded as a magazine.

Earl "Butch" Graves, Jr., CEO of Black Enterprise, is transforming the media company his father founded as a magazine.

Growing up in the black community in Brooklyn and Washington, D.C. in the ‘70s and ‘80s, there were a few things you'd take for granted: 

We learned Lift Ev'ry Voice and Sing, also known as the Negro National Anthem, in school. We learned there was practically nothing George Washington Carver couldn’t do with a soybean. And a middle class black family was likely to have at least four magazines in the house: Ebony and Jet, of course. And if they were a little fancy, Essence and Black Enterprise.  

These days, magazines aren’t what they used to be. (See Meredith Corp.'s purchase of Time Inc.) Like many digital publishers, Black Enterprise is undergoing a reinvention, becoming less a publication and more a live events business. Back in October I interviewed Intel's CEO at a Black Enterprise tech event outside San Francisco – an event that showcased the brand's push to evolve beyond the printed page. 

Earl Graves, Jr. – he's known as "Butch" – is the son of the founder of Black Enterprise. Now he's the CEO. I sat down with him to talk about how the brand was born, how it's trying to evolve in a digital world, and what the future looks like for minority entrepreneurs.

53: Fixing the Shopping Experience with Tech: Katrina Lake, founder and CEO, Stitch Fix

 
Katrina Lake is the founder and CEO of Stitch Fix. At 34, she is the youngest woman ever to take her company public.

Katrina Lake is the founder and CEO of Stitch Fix. At 34, she is the youngest woman ever to take her company public.

Katrina Lake is the founder and CEO of Stitch Fix. And as of today, at 34 years old, she is the youngest woman to take her company public – ever.  

Stitch Fix is a San Francisco company that combines data-crunching computers with human stylists on a mission to send you the perfect outfit. On Friday the company went public on the Nasdaq stock market at a market value of more than $1 billion, and I was there for CNBC, covering the remarkable story. 

Lake sat down with me at the Nasdaq in Times Square minutes after shares of Stitch Fix started trading for the first time – you can hear the buzz of Stitch Fix employees and customers in the background as we talk. The first part of our conversation was live on CNBC's Squawk Alley, which I co-anchor weekdays on the network. She took some time after that portion to talk more about how she developed the idea for the company, why she still works as a stylist on the platform, and why the story of how she overcame sexual harassment from an investor is especially resonant today. 

Some highlights:

On why she started Stitch Fix:

"I love retail – it's a huge, meaningful category – it's like a $350 billion category that's growing. And yet only 15% of that is bought online. So I looked around and I was like, however people are going to buy clothes 15 years from now, I want to be at that company. And I looked around, and I just didn't feel like I saw that."

On where the entrepreneurial itch came from:

"I wasn't the kid that had a lemonade stand growing up. My mom is a public school teacher – she just retired, she was a public school teacher. My dad is a doctor in the public system. We didn't have a super-capitalist household. I always imagined that maybe I'd be a doctor. For me, it just ended up being this opportunity. I want to work at the retailer of the future. When I didn't see it, I realized that I could start it myself."

On the sexual harassment she had to deal with from an investor while building her company:

"My path as an entrepreneur hasn't always been easy. I've learned a lot through that. My hope is that now that there's such a broader conversation about the challenges of many people in many industries beyond tech, my hope is that the conversation moves things forward."

She had more to say about that – and a lot of other topics – on the podcast. Have a listen.

52: From Marine to Tech IPO Founder: Bringing a Sense of Mission to Leadership: Bandwidth CEO David Morken

 
David Morken started Bandwidth when he was leaving the Marine Corps 18 years ago, and just took it public on the Nasdaq.

David Morken started Bandwidth when he was leaving the Marine Corps 18 years ago, and just took it public on the Nasdaq.

Hot technology companies tend to be based in Silicon Valley. They tend to be founded by eager undergrads or Harvard or Stanford business school alums. And these days, their leadership tends to lean strongly to the left politically. 

Bandwidth is different.  

Bandwidth is a business communication software company based in Raleigh, North Carolina. Co-founder and CEO David Morken served in the Marine Corps and went to law school. And he doesn't hide his Christian faith – while he says he also encourages his employees who have different belief systems to be authentic at work, too. 

Bandwidth had its IPO on the Nasdaq on November 10, the day before Veterans Day and birthday of the Marine Corps. Morken timed it intentionally. The company is worth more than 300 million dollars, and Morken is determined to keep it independent and based in North Carolina. We talked about how the Marines prepared him to be an entrepreneur, why he believes student debt is a drag on the country's future, and how he handles today's divisive culture wars. 

51: The Cloud Wunderkind Turned Veteran: Box CEO Aaron Levie

 
Aaron Levie and his friends founded Box when he was a 20-year-old college student. He dropped out. It's now worth about $3 billion.

Aaron Levie and his friends founded Box when he was a 20-year-old college student. He dropped out. It's now worth about $3 billion.

It’s a familiar story in tech history: college friends stumble onto a big idea, drop out to pursue it, build a company, make mistakes, and eventually take that company public and make millions of dollars. That’s Apple, that’s Microsoft, that’s Facebook – and that’s Box.  

Aaron Levie is the cofounder and CEO of Box, a company founded at the dawning of the cloud era. The basic idea: Wouldn’t it be great if we could store all kinds of digital files on the internet and teams could work on them at the same time, instead of emailing them around? 

The answer is yes. That would be great. And Levie and his friends built a company now worth nearly $3 billion proving it. 

The cloud thing seems obvious now, but when Levie was 20 years old and co-founded Box 12 years ago, it was far from it. I started covering him and the company in the early years of that journey, and I sat down with him days ago at the Nasdaq MarketSite in Times Square to catch up. At the wizened old age of 32, Aaron’s got a fresh take on advice he should have heeded, and where Silicon Valley needs to go next:

Why He Didn't Sell

Before Box went public, the founders fielded some interest from companies that wanted to buy them out. They had to talk about how they felt about it, and whether they'd sell.

"That sort of forces you to have the conversation of, 'What are we really in this for?'" he says. "We did these brainstorms for a few weeks – my cofounders – and in the brainstorms it was like, okay, let's say you did this. What would we go do next if we ended up selling? And actually everything looked worse than what we were doing."

That settled it. Levie says they've never had that kind of conversation about selling since.

Silicon Valley's Identity Crisis

Right now Silicon Valley giants' motives are in the spotlight, as Congress and a special prosecutor look at how Russia used social networks to try to influence the electorate leading up to the 2016 presidential election. I asked Levie about how tech leaders are handling the issue, and to what extent it calls into question the industry's approach to technology itself as inherently good.

"The founding stories of these companies are these fun, social things that are going to help people's lives," Levie says of Facebook, Google and others. "What happens is as they scale, you start to see the more pernicious use cases and consequences of these technologies. There's a zero percent chance that in the founding of Google, Facebook or Twitter there was a conversation about what if a foreign nation decides to use one of these platforms to impact the flow of information in our country."

But we're certainly talking about it now – and Levie gives great insight into how tech founders continue to think about these challenges.

50: The Man Who Helped Shape Gaga, Trainor, Legend: Troy Carter, Atom Factory & Spotify

 
Troy Carter grew up in West Philadelphia, and has developed a reputation for valuing artists the mainstream underestimates.

Troy Carter grew up in West Philadelphia, and has developed a reputation for valuing artists the mainstream underestimates.

When he was 14 years old growing up in West Philadelphia, Troy Carter started promoting parties at a neighbor's house and charging for entry. He did the DJing himself to save money. 

Today he's one of the most respected visionaries at the intersection of two industries: music and tech.  

Carter wears a lot of hats. He's been a manager, working with the likes of John Legend, Lady Gaga and Meghan Trainor. He's an investor, a general partner at venture capital firm Cross Culture Ventures. And he's a connector. As global head of creator services at Spotify, he's ushering artists into the streaming age. 

I met up with Carter recently outside of San Francisco at the Black Enterprise Tech ConneXt Summit. We talked about his path from rags, to riches, to rags, and back again – and how a high school dropout learned to reinvent himself, and an industry. 

What's Your Essential Difference?

Carter talks about seeing a passion – a cause – in an artist that he believes can set her apart. With Lady Gaga, it was outreach to marginalized youth who didn't fit into society's gender roles. With Meghan Trainor, it was giving a voice to women who didn't look like typical magazine cover models. And then there's the question of motivation.

"What are those soft things that I see in this artist that, absent a hit song, could push them over the finish line? Because artists ebb and flow. You're hot and you're cold," Carter says. "Do you have that natural ability, drive, where you're going to take a Mack truck and drive it through a cul-de-sac to see things through? In entrepreneurs, you're looking for the same thing."

It's a valuable question for non-entrepreneurs, too: What's essentially different about the creative spark that you bring to your work? What fundamentally changes when you're added to a team?

Look for the Gaps

Part of the reason Carter was able to break into the music scene was that he was promoting acts that established venues wouldn't touch. In the 1990s, that meant up-and-coming hip-hop acts.

"I was the first person to bring Jay-Z down to Philadelphia, Wu-Tang Clan down to Philadelphia, Notorious B.I.G. And I met P. Diddy through bringing B.I.G. down to Philly. That was sort of my relationship with the New York hip-hop scene. That was one of the things that took me out of the farm club and into the minor leagues, and kind of moved up from there."

Carter believed there was a broader audience for the artists, and that it was possible to put on profitable events that wouldn't descend into violence. Because he had learned to move in different cultural circles, he had the insight to build a career on it.

49: A Startup Betting on Human Intelligence: Rachel Carlson, CEO, Guild Education

 
Rachel Carlson's company, Guild Education, helps companies offer education as a benefit to employees.

Rachel Carlson's company, Guild Education, helps companies offer education as a benefit to employees.

In case you haven't noticed, there are some big challenges facing the American worker. Unless you're in the top 20 percent salary-wise, if you've kept the same job, chances are you haven't gotten a big raise in the last decade or two. 

The answer? There are arguments about whether a higher minimum wage would be a good fix, or a dramatic shift in tax policy. Rachel Carlson has a different idea. 

Carlson is the co-founder and CEO of Guild Education, a startup that helps companies like Taco Bell to offer college tuition assistance as a benefit to their employees. Carlson has a unique blend of experiences – working in government, starting companies in Silicon Valley, and going to school on the other side of the tracks as a kid – that give her an intriguing perspective. 

What About Education?

As Ray Dalio pointed out on LinkedIn this week, an enormous gap opened up between the wealthy and the rest of America, beginning in the 1980s. The picture for workers who don't have four-year college degrees is especially bleak.

Carlson at Guild Education is trying to make it easier for workers to go back to school with help from their companies. It's a win-win-win: Workers get help with their tuition, employers get better retention of their best workers, and colleges get access to a pipeline of promising students.

Community Colleges Are Getting Crushed

That pipeline is hard to come by otherwise. Carlson found that in 2014, the top U.S. buyers of Google ads were for-profit universities.

"They were spending $4,000 - $6,000 to acquire a student," she says. "What happens is, when the for-profits are spending that much, strong non-profit universities can't keep up to recruit the students they want."

And once a non-profit college spends the money to recruit a student but loses to a for-profit competitor, the money's gone. They don't get it back.

Working Students Work Better

One of the reasons Guild Education's offer is tantalizing for schools: It turns out that if an adult student is working, she or he tends to be a better student. It makes sense, if you think about it. She's already actively trying to improve her situation.

So what policies could amplify this effect, and get companies to invest more in helping their best employees get a degree? How did Carlson start Guild Education? And what in her past put her on the path to tackling this knotty problem? For that, enjoy the full Fortt Knox podcast episode.

48: The Beauty of a Calculated Risk: Chamath Palihapitiya

 
Chamath Palihapitiya was running AOL's instant messaging business at age 27. Not long after, he took a gamble on Facebook.

Chamath Palihapitiya was running AOL's instant messaging business at age 27. Not long after, he took a gamble on Facebook.

Chamath Palihapitiya is one of the most sought-after investors in Silicon Valley. It's because he has a knack for figuring out how things work. At Facebook, he led the team that studied our online behavior and figured out how to grow that service from 50 million users when he joined in 2007, to 700 million users when he left four years later. 

Now as the CEO of venture investing firm Social Capital, he's working on something different: cracking the code to understand how tech is changing our world – and maybe make a few billion dollars in the process. It's quite a journey for Palihapitiya. He grew up poor, an immigrant from Sri Lanka, with a knack for numbers, a talent for gambling, and the proverbial deck stacked against him. 

I visited Palihapitiya at Social Capital's offices in Palo Alto, California to get an up-close look at how he thinks. One of his deepest insights? Getting the right answer is overrated. Real growth happens from examining our wrong answers. 

Fitting in is Overrated

Palihapitiya grew up in Canada after his family immigrated from Sri Lanka and was granted refugee status. The family always struggled financially, but he didn't feel extremely self-conscious about it; instead, he adapted. He remembers that middle-class friends in high school in Ottowa were eager to gamble away quarters and dollars during lunch-hour card games; Palihapitiya quickly figured out that he would make the most money by setting up the amateur casino and acting as the house.

"I would take that money during the week and I would kind of go to these charity casinos and play blackjack. And I was a card counter back then. So I'd be spinning up my money," he recalls. "I didn't have a bedroom. I didn't have a bed. I had a mattress, and we used to keep it in the closet of the hallway. I used to take it out, sleep in the living room, put it back."

Penciling Out the Downside

Years later, working at AOL, Palihapitiya did a deal to integrate instant messenger with a fledgeling product called Facebook. (He had wanted AOL to try to buy Facebook, but the company was too tangled up in legal drama.) Eventually the partnership unravelled, and Facebook's teenaged founder asked Palihapitiya if he wouldn't like to leave the venture firm where he had taken a job, and join the startup instead.

"I said, 'What is the distribution of outcomes at Facebook?' Most of the scenarios were less than [I would make at the venture firm], but there were a few scenarios where I could make a case that it could be equivalent to what I would make at Mayfield over a four-year period, and in a very small number of cases it would be in excess," he says. But even if it doesn't work out, he thought, "I will have met some of the smartest people in the world, and I'll be in the game. And I will have learned something about myself, whether I can do something at a really early-stage scale."

As it turned out, of course, Facebook was a pretty good bet for him.

47: Tech's Prometheus Warns that We're in a WTF Moment: Tim O'Reilly, O'Reilly Media CEO

 
fortt-oreilly.jpg

Tim O'Reilly studied classics, and had never come in contact with a computer until after college, when a friend asked him to help write a technical manual.  

It's quite a turn, then, that he has become a Promethean figure in Silicon Valley. Like the mythical titan who stole fire from the gods and brought it to mankind, O'Reilly's efforts (including a publishing empire, conferences and learning platforms) have both demystified computer languages and presaged tectonic shifts. 

He literally wrote the book on the Internet, the Internet User's Guide & Catalog, the first popular tome about the subject. He and his events birthed terms like "open source" and "web 2.0," which have become enduring parts of the tech lexicon. His MAKE magazine arguably launched the broader maker movement of hands-on crafters and tinkerers. 

So naturally I wanted to sit down with Tim to talk about his new book, WTF: What's the Future, and Why It's Up to Us. In it, he has strong words for the Internet-driven tech industry he helped to shape, and some insight for workers like us trying to navigate the new digital landscape. 

46: Hit Refresh with the Power of Empathy: Microsoft CEO Satya Nadella

 
Microsoft CEO Satya Nadella joined me for EP. 46 of the Fortt Knox Podcast, on his journey and Microsoft's cultural revival.

Microsoft CEO Satya Nadella joined me for EP. 46 of the Fortt Knox Podcast, on his journey and Microsoft's cultural revival.

Satya Nadella is the third CEO of Microsoft. He's also a husband and a father of special-needs kids. He's an immigrant.  

And he's pretty close to doing something that, until he took the job just over three and a half years ago, most people in tech – heck, most people at Microsoft – thought was impossible. 

That near-impossible task is a cultural revival of a once-dominant tech giant that was losing its grip on its soul. Under Nadella's leadership morale is up, and so is product quality and the stock price. The question is whether all of that can stick. 

Satya sat down with me at the Nasdaq Marketsite in Times Square in New York, where he stopped through to promote his new book, Hit Refresh, about the revival he's attempting at Microsoft. The conversation for my Fortt Knox podcast offers a fresh look at one of the most influential technology leaders in the world today, who's engineering a cultural rebirth few thought possible – while also being a dad who faces some unique challenges helping his kids reach their full potential.  

To do it all, he's made some decisions that go directly against popular wisdom. Some highlights: 

Downgrading His Green Card

As a young engineer at Microsoft, Nadella faced a quandary. He was ready to start a family – but with his green card, he wouldn't be able to bring his wife Anu over to the United States. An immigration lawyer at Microsoft suggested a move that seemed ridiculous: Give up his coveted green card, and get an H1-B visa, which allows spouses to enter the U.S. I asked him about the story he recounts in the book, and how it influences the way he looks at today's immigration debate.

"A comprehensive immigration reform—that again, speaks to our interests as a nation, what makes us stronger, what makes us more competitive, I think is much needed," Nadella said. "The idea that you have to give up your green card to get an H1-B is, in retrospect, silly. And so therefore let us in fact take the reform so that it works for us, both our security but as well as our competitiveness."

Showing His Hunger

When he was one of several candidates to be the next CEO, one of the Microsoft board members who would pick the successor pulled him aside. If you want the job, he said, you have to act more like you're really hungry for it. Outgoing CEO Steve Ballmer dismissed that notion, saying it's too late to act like a different person now.

"It was not like we were sitting around, thinking that Steve is going to retire. So it was a shock. And the board did the right thing, which is they looked far and wide," Nadella said. "When they came and talked to me and they said, 'Do you wanna be CEO,' I was honest. I said, 'Only if you want me to be CEO.'"

That, of course, goes against all the advice in the business books, self-help books, and self-esteem books. But Nadella wasn't lacking in confidence – he was just bringing a different style, a different humility, to the job.

Leading With Empathy

One of the more personal angles in Hit Refresh – and in my conversation with Nadella – concerns his journey as a father. His son Zain was born with cerebral palsy, a challenge that forced him to change the way he looks at relationships not only at home, but also at work.

"A few years went by and then I realized nothing happened to me. Something happened to Zain," Nadella said. "What's my responsibility as a father? I think that was perhaps one of, you know, the big hit refresh moments when I look back for me personally, that has influenced. And so, I think it's our life's experience that then leads into work, and work's experience that leads into life. And it's one of those things where, it has to be lived. We can't be taught about it."

Today's corporate cultures can sometimes glorify a take-no-prisoners approach; but that's not the only way.

45: The Storyteller's Dilemma: Avid CEO Louis Hernandez, Jr.

 
Louis Hernandez, Jr. credits his parents with opening up opportunities that allowed him to dream big.

Louis Hernandez, Jr. credits his parents with opening up opportunities that allowed him to dream big.

Louis Hernandez Jr. is the CEO of Avid Technology, a company that makes tools for editing video and audio, and writing music. 

Avid is facing hard times as rival Adobe grows stronger with Premiere and other creative suite tools, and as more software moves to the cloud. 

Hernandez is unique for a lot of reasons. One of them is that he's the Latino CEO of a publicly traded technology company. He recently wrote a book, The Storyteller's Dilemma, about the way technology is changing the media market.  

Louis talked to me about his path to the C -suite, his vision for the future of storytelling, and the factors that made his story so different from many of his cousins in the L.A. area where he grew up.

44: Don't Try to Find an Easy Time to Do Hard Things: Daily Harvest founder Rachel Drori

 
Rachel Drori founded Daily Harvest to solve the problem of getting nutritious food that's also quick to prepare.

Rachel Drori founded Daily Harvest to solve the problem of getting nutritious food that's also quick to prepare.

Rachel Drori comes from from a long line of entrepreneurs – her immigrant grandparents started a business when they got to the United States.  

Even more unique: Her mother started a business too, so she grew up around women founders.

Today she's the founder and CEO of Daily Harvest, a young startup that sits at the intersection of nutrition and convenience. You think starting a business is hard? Well, it is. But Drori started Daily Harvest when she was seven months pregnant, then raised investment funds for the business when she was pregnant. Her story is instructive for anyone who has wondered whether now is the right time to take a big career leap.

I sat down with Drori at the Nasdaq MarketSite in Times Square to get insight into a number of questions, including: Is there ever an easy time to do a hard thing? I think you'll come away with a fresh appreciation for what you can get done if you've had the right preparation.  

43: From Orphan to Entrepreneur: Musanga Logistics CEO Njavwa Mutambo

 
Njavwa Mutambo says he was orphaned at age 7, but that hasn't stopped him from working to build the tech startup scene in Zambia.

Njavwa Mutambo says he was orphaned at age 7, but that hasn't stopped him from working to build the tech startup scene in Zambia.

Njavwa Mutambo is the CEO of Musanga Logistics, a delivery company in Lusaka, the capital city of Zambia. 

Technology has the potential to transform economies in Africa, empower small businesses, lower costs – but before any of that can happen, there are some basic challenges. One of those is the cost of delivery. 

That's where Njavwa, and Musanga Logistics come in. He's using bicycle couriers and people who own trucks and need side-work, Uber-style – to connect people in Zambia like it's never been done before. 

Mutambo is by far the youngest guest I've ever had on the Fortt Knox Podcast. I met him by chance during a visit to Silicon Valley this summer. I was giving a talk at a venture capital firm, Goodwater Capital, and he was there. He asked me about coverage of African startups, told me what he was doing, and I just had to hear more. 

And that's really a big part of what Fortt Knox is about – that's why it rich ideas and powerful people. Whenever I can talk to someone who's doing something extraordinary that shifts the way I think about business, achievement, making the world better, I want to bring you that. 

So I invited Njavwa to CNBC's bureau at One Market Street in San Francisco. He described his vision for bringing more sophisticated e-commerce to the African continent, his path from impoverished orphan to tech entrepreneur, and what he learned from seeing Silicon Valley – and America – up close for the first time. 

42: Starting A Business? Your Most Important Partner Might Be at Home: Ben Chestnut, MailChimp

 
Ben Chestnut started a digital greetings company after getting laid off from a web design job; then, he started MailChimp.

Ben Chestnut started a digital greetings company after getting laid off from a web design job; then, he started MailChimp.

Seventeen years ago, life gave Ben Chestnut the push to start the company that became MailChimp. 

He was in web design. He got laid off. His employer offered him another job, but he knew – this was his chance to build his own thing.  

Today if you run a small business or you're into marketing, you've probably heard of MailChimp. For everyone else – it's the way a lot of people reach their customers' email inboxes. Newsletters, offers for special sales, you name it – MailChimp is in the tricky game of helping companies reach the people who actually want to be reached. 

Now, Ben Chestnut's team has more than 14 million users, and had more than $400 million in sales last year. Ben himself is an introvert – a soft-spoken guy who has perfected the art of capitalizing on the wrong answer and getting to the right one. 

The fateful moment when Chestnut decided to strike out on his own? He and his would-be cofounder scheduled a dinner out, and invited Chestnut's wife.

"She knew that deep down inside, I needed to start a business one day in my life. And so when I was laid off, and my cofounder and I really wanted to start a business, I said 'I've got to get my wife's permission first,'" Chestnut recalls. "And so we all went out to dinner one day, and I remember asking her, and to her it was a no-big-deal kind of thing. She just said, 'Yeah, do it. You need to do it." And that's all I needed to hear."

Even so, the road wasn't easy. First, the young company focused on web design. After a while, it became clear that what the small businesses really needed was a way to keep in touch with their customers. Eventually, MailChimp was born.

41: How a Master of Scale Climbed to the Top: Reid Hoffman, investor & entrepreneur

 
Reid Hoffman is co-founder of LinkedIn, early investor in Facebook, board member at Microsoft, and a member of the "PayPal Mafia."

Reid Hoffman is co-founder of LinkedIn, early investor in Facebook, board member at Microsoft, and a member of the "PayPal Mafia."

There is no one in Silicon Valley who's more connected than Reid Hoffman. That might be because he plays all of the connector roles, sometimes at once.  

He's a venture capitalist, at Greylock. He's an entrepreneur who co-founded LinkedIn, and sold it for $26 billion last year. (Hoffman's net worth is estimated to be north of $3 billion). Now he has a seat on the board of directors at Microsoft. After teaching a class at Stanford, he started a podcast, Masters of Scale, that's about the art and craft of building monster businesses.  

Hoffman is deeply qualified on that subject. He was a founding board member at PayPal, and early on became its chief operating officer. That also makes him part of an eclectic group of characters known as the "PayPal Mafia" former PayPal employees who went on to dizzying success. Members include Elon Musk, YouTube founders Steve Chen and Chad Hurley, investor Peter Theil, and entrepreneur Max Levchin, to name a few.  

I spent some time with Hoffman last week when I flew out to San Francisco to moderate a LinkedIn debate in front of a live audience. It wasn't politics: Reid was debating his friend Tim O'Reilly on the merits of spending gobs of investor money to build startups into dominant forces. 

After the debate, Reid sat down with me on the 17th floor of LinkedIn headquarters to talk about how he scaled from a pre-teen who was ambivalent about school into one of tech's most prolific builders:

That F in French 

In late elementary school, young Reid didn't see the point of class. That might explain how he ended up failing French.

"Once I started realizing I want to build that, I want to accomplish that, I want to participate and help in that kind of mission, in that kind of project, oh – this learning helps me do that. And once I made that connection, I got very focused on learning."

The lesson: Some people need to connect with more than the task if they're going to build great things. They have to see the big picture.

The Case for Diversity  

Hoffman has engaged in the rising conversation about culture and fairness in Silicon Valley by recommending a "decency pledge" that investors would make to founders. It's a subject I've explored with a number of Silicon Valley luminaries lately, as the tech capital's meritocracy facade has shown some cracks lately. 

"You have to start with a recognition that we are not yet the meritocracy we want to be. We are not yet the diverse and inclusive society we want to be. And we should all work toward that together," Hoffman says. How? "Make sure you're putting energy into helping the right high-talent, diverse individuals learn the culture. Whether it's anything from doing podcasts or other things to mentoring or teaching classes."

A Downside of Experience  

It turns out experience isn't everything. In one area in particular, it may have hurt Hoffman's investment portfolio. 

"Knowing all of the ways that PayPal almost died in getting its creation makes me know what the checklist is of, how are you on all these minefields? And so I didn't invest in Square, which is obviously a mistake. I didn't invest in Stripe, which is obviously a mistake. Great founders, great, interesting companies. It was my own PTSD from PayPal."

It's yet another lesson Hoffman has learned – and shared – that involves letting diverse points of view into the room, and remaining open-minded. That is, if you want to grow.

40: Another Way to the Top: How Julie Sweet Built Her Own Ladder

 
Julie Sweet, CEO for North America at Accenture, has honed the art of learning skills that prepare her to leap ahead.

Julie Sweet, CEO for North America at Accenture, has honed the art of learning skills that prepare her to leap ahead.

Julie Sweet was a high school sophomore with the gift of gab, entering various debate and speech competitions for the prize money, building her own scholarship fund. She wasn't doing it for kicks; at times growing up in Southern California she had just one pair of shoes, or one pair of pants that fit. Her father painted cars for a living, and her mother was a hairdresser.  

One particular contest at the Lions Club had come down to a final showdown between Julie and another girl. Julie lost. Stung by the injustice of it – she felt her speech had been better – she griped to her father on the way home.  

The other girl had been cutesy in the way girls were so often expected to be, that way Julie herself never had been. Plus, the girl's dad was prominent in the Lions Club. "My father said to me, 'You have to be so much better than everyone else that it doesn't matter about connections, it doesn't matter who you're the daughter of. And you weren't.' And so essentially, stop whining."

Julie Sweet today leads the North American business at Accenture, a global consulting giant that employs more than 400,000 people and produced more than $32 billion in sales last year. Sweet's territory made up almost exactly half of that total. 

I'm not really sure of the ideal way people become consultants. Maybe they get good at something, then show other people how to do it better? 

Sweet's path was different. She was a lawyer – a partner at one of those swanky firms: Cravath, Swaine & Moore – and left that to be the top lawyer at Accenture. 

She then parlayed that job into a bigger job. And that's the key detail here. She has a history of doing that sort of thing, and for the Fortt Knox podcast, I wanted to find out how. 

 

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.