Venture Voice – interviews with entrepreneurs
24 episodes
Jessica Lessin of The Information turned her journalism beat into a business
Jessica Lessin is founder, CEO, editor-in-chief and sole owner of The Information, the influential subscription-only tech publication that was launched on a simple idea: write deeply reported articles about the technology industry that people won't find elsewhere. As she shares in this episode, like many who work in the news business, she got the journalism bug early on, working on school papers and enjoying the permission it gives you to “be a little bit nosy.” While at Harvard, she covered the faculty beat for The Harvard Crimson, something she likens to covering Congress. Oh, and there was also “the other thing that was going on” — the launch of Facebook. Jessica went on to cover a new emerging tech beat for The Wall Street Journal, writing about startups and “what the kids were doing online.” But she had trouble convincing editors that companies like Facebook were worth writing about. She says they simply didn’t understand the business models that would ultimately propel these companies.
Like many entrepreneurs, Jessica saw an opportunity within a disruptive moment. She was convinced that there was a broad audience for a business publication that focused on deep reporting around technology. As publishers tried to chase a business model based on “eyeballs and clicks,” she decided to develop her own model that would build and monetize audiences based on quality information. Jessica Lessin just celebrated the 7th anniversary of The Information, and it’s clear that her business model and her thesis — that you can’t remove business from the context of technology and disruption — are more relevant than ever. Tune in to hear more about what she learned covering tech startups and how it informed the launch of her own tech news startup.
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Todd McKinnon's journey taking Okta from $0 to a $25+ billion public company
I can still remember logging in to PeopleSoft at my first job to see what deductions had come out of my paycheck. Now, all these years later, I’m interviewing the man who wrote that very code. Todd McKinnon, my guest on this episode of Venture Voice, began his career at PeopleSoft before moving on to Salesforce and ultimately founding Okta. Todd’s company is now worth over $25 billion. This episode takes you on Todd’s entrepreneurial journey, from the Powerpoint deck he presented to his wife (subtitle: “Why I’m not crazy” for quitting my job at Salesforce) to the initial product idea (with a name that sounded “like a French perfume”) to successfully completing an IPO. Listen now on Apple Podcasts.
“You had to be able to have enough confidence that you’d be able to build this iconic tech company around this initial idea. A lot of initial ideas — people will pay for them but they don’t have that long-term staying power. They become a feature.”
Todd McKinnon is the founder and CEO of Okta, a $25 billion publicly traded software company that you may never have heard of, but it solves one of the most annoying 21st century problems: having to remember all of your various log-ins and passwords. Thousands of companies use Okta Identity Cloud to manage access and authentication for their employees.
I can relate to Todd’s experiences as a scrappy entrepreneur and the challenges of founding and growing a business. My job as CEO has changed tremendously as my own companies, Muck Rack and The Shorty Awards, have grown from just a few employees to about a hundred today. I wanted to learn how Todd scaled to thousands of employees.
“I think I try to combine the best parts of Salesforce and the best parts of PeopleSoft and throw in a little bit of my personality on the side, and let the chips fall where they fall.”
As you’ll hear in this episode, Todd got his first taste of what technology can do for customers while working at PeopleSoft. From there, he moved on to Salesforce, where he had a front-row seat to the early days of SaaS — as well as the opportunity to work for Mark Benioff before he became a multi-billionaire. Todd was the first person to lead the Salesforce engineering team, scaling it from just over a dozen people to hundreds. Those professional experiences and the cultures of the two companies would stick with him and inspire many of the decisions he made as he embarked on his own start-up journey.
“There was part of me that wanted to be the boss, and part of me that wanted to attack the challenge of creating a company from scratch, knowing that the odds are very long… I couldn’t be the person who didn’t take a shot.”
Todd points out that whenever there’s a big disruptive technical shift — like the transition to the cloud — there’s an opening to build a new business. And young companies, which don’t have all the baggage of the bigger, more established players, are often better positioned to take advantage of that opportunity. Still, the odds are long. So when he sat down to sell his wife on the idea of quitting his very good job at Salesforce to start his own company, he says he “did what anyone would do, you know. I wrote her a PowerPoint deck presentation.” The deck included nine slides that explained how, when it didn’t work out, he could just get another job. Fortunately, though, he didn’t end up having to fall back on Plan B.
“As a CEO, my decision-making process really slowed down…you have to make sure that you get involved in the right decisions, you don’t overly involve yourself in all of them. And you have to be ready to make them.”
Now matter how much experience and insight you have from working as a leader in a big company, you’re going to encounter a steep learning curve once you start scaling your own business as its CEO. I was interested to hear how Todd adjusted to that role and how he grew into the job. As he shares, he had some good advisers on his side, but he also had to face the reality that he didn’t have all the answers — and that not having all the answers was ultimately a good thing. It helped him build the kind of collaborative culture he wanted, where employees have a stake in the decisions.
“It was very important that the company, while we celebrated [going public], that the company didn’t use it as a reason to stop pushing or a reason to be satisfied.”
Todd likes to compare the experience of going through an IPO to high school graduation. It’s a rite of passage, but you don’t want it to be the best day of your life. Like many entrepreneurs, Todd is motivated by challenge, and he is always on the lookout for the next big wave on the horizon. While it was challenging to build a successful business, he’s energized by the thought that the biggest challenges are still ahead of him — and so is the opportunity to build “an iconic technology company that will be remembered for decades in the future.”
Venture Voice – interviews with entrepreneurs
Muck Rack & Shorty Awards cofounder/CEO Greg Galant interviews the world's best entrepreneurs and creators, including the founders of LinkedIn, The Vanguard Group, Yelp, Brooklyn Brewery, Trello, Twitter and Stack Overflow.
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