Context Relevant CEO Stephen Purpura is working on the leading edge of big data — helping companies use their data more effectively. But Purpura, whose company scored $21 million from Bloomberg Beta, Madrona, Vulcan and others earlier this year, followed a career path many of his peers advised him against.

After working at Microsoft, Purpura decided to go back to school, earning a degree from Harvard and studying at Cornell before returning to found his own company. He describes being CEO of Context Relevant as “one of the most exciting things that I could do in my life.”

At Context Relevant, Purpura and his team are leaders in the field of big data and automated machine, exploring a space few other companies have investigated so deeply. Explaining why he loves his position, Purpura says the big idea behind Context Relevant is “to analyze data without hiring an expert.” [1:40]

Though an executive now, Purpura’s focus has always been on the technical. He explains that he wanted to be more than an “empty suit” who couldn’t explain how a product worked. “The only way you can do interesting new things and really explore the space is to get in and do it, he says. He adds: “If you do not understand [the tech], it is really difficult to lead a team effectively.” [6:40]

Before he was a startup CEO, Purpura spent several years at Microsoft, though he knew he wasn’t meant for that environment for long. “At bigger companies I sort of felt stifled,” he explains. As a CEO, “I get more ability to…be my inner child, in the sense that I get to do what I want as long as I can back it up and actually make it happen.” [9:00]

On leaving big companies to pursue further education, Purpura explains that many of his technical peers told him he was making a mistake. “Many people believed it was a blunder for me to go back to school,” he says. But he counts this time as a blessing. “Let’s face it: when you work at Microsoft or when you work in the industry, you sort of get a point of view, and you put blinders on that point of view. And what I was able to do in the middle of my career was redefine my point of view.” [11:00]

When asked if he had advice for other startup founders, Purpura emphasized the importance of being in the right market. He shared a story from an earlier startup where they failed to find a big enough market for their product, from which he ultimately learned that it’s better to find a great solution to a problem in a big market than to focus on finding the right team or the most money. “Even if you have a fantastic team with $100 million in cash, it’s difficult to fix the market,” he said. “If the opportunity is large enough, you will find people who want to work on it” even if you have to bootstrap on the weekends.

Purpura closed the interview with thoughts on life as a founding CEO. He describes his company as “an overnight success story that took 13 years.” “You are responsible for everything and there is nothing going for you,” he says, adding that it’s the hardest job he’s ever had in his life.

Former Seattleite Jon Jenkins, the Head of Engineering at Pinterest, has taken the lead of a “super scrappy, super agile” team of engineers building one of the biggest social networks on the web today. Using billions -- or maybe even trillions -- of data points supplied by users around the world, he and his team are curating personalized experiences for every Pinner, helping to show them new things they didn’t even know they liked yet. I sat down to talk to Jon about solving some of the most exciting challenges of his career in this edition of Nextcast; here are a few of the highlights:

This PolySci graduate with a knack for “hacking around” has done the big company and the startup thing more than once in his career. After spending almost 9 years at Amazon in Seattle, he hightailed it to San Francisco to join the Pinterest startup team, who piqued his interest with an intriguing set of problems to solve. Jenkins says he is “fascinated by challenges associated with scaling things...and challenges associated with data mining or deriving useful information from large pools of data.” He adds, “Pinterest has both of those challenges at an even bigger scale.” (4:30)

The problems Pinterest is solving for its users are based on huge amounts of data providing huge amounts of value to customers, who may not even know they want that value until they get it. “A pin is an object...coupled with the user’s context about that object,” Jenkins explains. It’s not just about what gets pinned, but what it says about the Pinner’s interests. Jenkins and his team are using that information to present that user with even more things they might enjoy, even if the user doesn’t know they like it yet. “We can tell you things about yourself that you didn’t even know,” based on what you pin, within the context your boards and profile. “That’s something I don’t think anyone has done before.” (7:20)

Jenkins shares that his business philosophy is based on always putting the customer first. “In no matter what you’re building, you should absolutely understand how it’s going to positively impact...customers,” he says. If you can’t articulate that in a way a customer will understand, he says, you’re not likely to be successful. He feels just as strongly about APIs -- which helps to explain why there is no Pinterest API yet. “APIs are forever, and you need to treat them that way. You don’t get to release these things to the world and then pull them back, or at least you shouldn’t.” Jenkins adds: “Software is a promise.” (12:02)

Though he still loves Seattle, Jenkins admits he wishes he’d moved to San Francisco earlier. The vibrant, connected, sharing-focused community is something he would like to see carry over to other tech communities. Another thing he wishes? That’d he’d pushed himself harder, earlier in his career, to take more risks. “Being successful in technology is really about pushing the boundaries,” he says, advising tech upstarts to not let a fear of failure control them. And though risk-taking and idea-challenging are now part of his daily routine, he explains, “I should not have been afraid to break things or challenge conventional thinking earlier.” (17:00)

Jon’s advice to other startups and leaders is concise, but powerful. “You better understand what your customer wants,” he says first. “[Be] incredibly pragmatic in how you deliver,” is his second tip, which is all about the power of fast iteration and agility. The quicker you can notice problems and do something about them, the better off you are. And finally, he says: “[Build] an engineering team that actually wants to deliver stuff.” Not every engineer gets excited by shipping, but you need to make sure your team is staffed with only that kind. Getting your product in front of customers is the difference between success and failure. (24:25)

Though he’s only held one other job since college, WhitePages founder and CEO Alex Algard thinks he’s found a pretty good fit in his growing company. “I like the feeling of making an impact and a positive difference in the world,” he says of his role running a site that boasts over 50 million monthly users who come to them for contact information. And it’s not hard to see how he translated this into his role running a company based on delivering “directory assistance to the masses for free”.

He has learned a lot along the way, from why getting rid of investors might just be the best thing you can do for your business to how being a great leader makes great products possible. Here are some of his top lessons that he shared with Nextcast.

“We’re in collective denial,” Algard jokes about his now 10+ year old business. “If you look at how we do business...we have much more in common with how startups do business and how startups interact team-wise.” What this means is that despite having a team of over 100 people, his number one priority is still innovation and creating amazing products for their customers above all else.

Part of the company’s focus has come from getting rid of their external investors. “We still have a rockstar board,” he explains, but he adds that external investors by their very nature have different priorities for your company than you do. Their first priority is to their partners; as a CEO, your first priority should be to customers. “Sometimes it can be a little bit distracting to have a whole bunch of different people to report to as far as investors and employees and customers too.” After buying out his investors, Algard says his board conversations now aren’t about investment decisions, but about how to run the business even more effectively. (4:30)

“Nothing’s better than working with great people,” Algard says. His team at WhitePages works hard to maintain an incredibly high bar for talent, though “it’s absolutely a war for talent out there.” However, he has found power in his network to bring him the best of the best. “I think a lot of our best recruits came from networking,” he explains. And when it comes to keeping great people around? “We can’t over-invest in keeping our employees happy and productive.” (15:30)

What would Algard tell his younger self, if he could? “I would advise myself to focus on...lifelong learning. Don’t optimize your career on your 1 or 2 year timeframe; optimize it on a 10 year timeframe.” He adds: “It’s much more about the learning, it’s much more about the people that you work with” than necessarily making the biggest paycheck. (17:15)

Be sure to stick around for the end of this video where Algard reminisces about the time when WhitePages was recruiting one of their first-ever full time engineers. It’s a hilariously cringe-worthy look back on the startup days of a now established and growing company. As the company launches WhitePages PRO, their growing B2B unit, and continue “building a contact graph that maps out how people and businesses in the world are connected based on contact information” there are certainly many more good days and good stories to come. (20:45)

As a one-time English PhD student, Janis Machala didn’t always know her career would lead her down a business path. But now she helps other people pursue their passions and get the education they need to achieve their dreams, as the Executive Dean of Continuing Education at Bellevue College. On this edition of Nextcast, I interviewed Machala and learned how technology is changing education and why working at a big company might be a better first job for recent graduates. Plus, Machala shares her tips for creating an amazing startup culture.

“I never thought of myself as a business person,” Machala says. But when a friend referred her to her school’s business school as a possible avenue for jobs, she found herself enrolling in an MBA program, eventually specializing in marketing. “I loved the complexities you get in the marketing field.” (2:00)

Once she entered the workforce, Machala began working in textbook publishing -- an industry which, at the time, was struggling with how to integrate software and CD-ROMs into their products. “Nobody knew what to do with software,” Machala explains. A natural risk-taker, Machala volunteered for every opportunity to experiment with the new technology. “I found that making things up where there hasn’t been a hundred year history...is much more my style, she said, adding, “I realized the technology field was probably a great place for me.” (4:00)

Machala has worked at companies big and small across many industries, and has learned the importance of culture -- and why it’s more than ping pong tables and beer fridges. “So few people take a job for salary. Most people take a job because they believe in what that company’s doing,” she says. “Founders need to understand that they need to market to their talent.” And it’s not all about money. She notes, “Amazon is pretty frugal. It doesn’t stop them from recruiting talent.” (7:50)

“I think technology is going to radically change education,” Machala says. “Not only are we going to have this integrated offline-online world, but there’s going to be some fundamental analytics and big data elements” which will allow teachers to have early warning for students who are falling behind. She is curious to see how online education solves its current culture problem: students don’t form the same friendships and teams they do in in-person classes. “People have to know themselves,” she says, before trying a course online. (9:00)

Her advice to young founders and businesspeople is simple: “be willing to take calculated risks.” She adds that much of her success is due to being “willing to jump in and learn about something and not accept the status quo.” She adds that listening is just as important as talking. “You learn more by hearing what the needs are than by assuming what the needs are.” (13:35)

Machala says she advises students who are considering startups for their first jobs to first spend some time at a big company. A big company is “a great learning environment”. When you are just starting out, you have no sense for what is a good company, a good financial model, a good marketing strategy. Get your baseline education at a big company, and the innovate when you’ve got the necessary basics down. (20:00)