Age versus Experience

Age Ain’t Nothing but a Number…

The two companies in the national spotlight the last couple of weeks, Snap (aka Snapchat) and Uber have some things in common. Chief among them has been a constant questioning of whether or not their leadership is qualified to run what could be Fortune 500 companies.

Both have faced calls to add “experienced executives,” insider parlance for adult supervision. Both have seen execs come in for short spells before departing. This has also happened to company’s such as Twitter, as well.

The problem in many of these instances is usually viewed from the outside as an issue of age difference. You hear this sometimes from people who either make a bad hire, and try to excuse it, or from those who move from a corporate or established entity to a hot young startup.

But there is something a bit more complex going on here. And so I spoke with a bunch of CEOs who are on the young side, younger than 35, to dig into how they’ve felt in these situations.

Most admitted that figuring out how to work with older more experienced employees had less to do with a difference in age than it does with a gulf between the experiences of CEOs and their charges. And there seems to be no way to avoid this very challenging part of running a startup.

Whether it is a VP or C-level employee hired to help in a new stage of growth for a venture or whether it is someone put in place by a board of directors or VC, this seems to always be a thorny situation.

As VentureApp CEO Chase Garbarino described it, “I fucked this up multiple times.” And he’s not alone. Almost everyone I spoke with said some version of the same thing.

One reason, as Garbarino explained it is that hires who typically come from corporate world don’t realize that the title they hold in their former established companies is not comparable to what might be described as the same role in a startup.

And this can cause confusion for both a young CEO or an experienced new hire. As Garbarino described it, “The CEOs don’t understand from day to day what they want and what this person has been doing.”

Tom Coburn, CEO of Jebbit, says one of the issues between young founders and experienced execs working together can be cultural. As his company has grown, he said he’s made some mistakes but learned from them to change how the company works.

An Coburn knows well how a vast cultural difference can slow a company. In its early days, the entire Jebbit team, all in their early twenties, lived in a single house together. When they made a few older hires as they grew, they made mistakes they didn’t even realize Coburn said. “We’d work all day and then go home, have a beer, and then start talking strategy again to late in the night,” he explained. “We would make key decisions.”

Later, another member of the team who didn’t live in the house pointed out how that type of operation could lead to issues. Some folks who were supposed to be key stakeholders, but who might have other responsibilities (part-time jobs, families) felt left out of process and started to get upset. “They were right,” Coburn said, “we just didn’t realize the impact of the way we were working together at the house.”

So Coburn made changes. The only time they have tactical meetings is at 4:00. No more decisions made in casual environments. There had to be a strict separation of home and work.

This can be hard for young founders for other reasons. As Drizly CEO Nick Rellas told me, “When you are 23 or 24, you want everyone to be your friend. It takes time to realize that you need to be the steward of the business and what it means to be the boss.”

“I had to figure out how to be an asshole,” Rellas added. “But I wasn’t ready for that at first.”

“People don’t want to talk about this because it’s sensitive,” Chase Garbarino told me. “The difference in culture thing is real even if people don’t want to talk about it.”

As Garbarino explained, he feels like, after having run Bostinno/Streetwise Media and now VentureApp, he’s had the experience of being the young CEO and now has a bit more experience to avoid some earlier mistakes.

He’s 32. And has already built two companies, raise venture funding, and sold Streetwise. Experience is the key, and only comes with time, whether that be 10 years in business or 25.

Boston’s younger CEOs will continue to screw up. But, they are getting older and wiser. Should be fun to continue watching their development.

Who is under-the-radar?

In this week’s under-the-radar, we dig into a company that is under-the-radar from a VC firm that has been under covered as well.

I recently sat down with Vivjan Mytro of Hyperplane VC, who is leading one of the next generation VC firms in town. Hyperplane is involved in some major deals in Boston that are heavy on tech and long on potential impact including Talla, Indico, TellusLabs, and the previously mentioned Vesper, among others.

According to Mytro, the company in Hyperplane’s portfolio that is not getting enough attention is Volta Networks.

The reason? It might be that Volta, officially a “Routing-as-a-Service” platform for the cloud, is an old school-type of Boston tech company. What that boils down to is that its tech is complex — bringing routing to the cloud and distributing routing intelligence between processes — in a way that could improve networks and infrastructure for the booming spaces of machine learning, the Internet of Things, and sensors.

“These guys have had some major validation recently from their big customers,” Mytro said. “This could be pretty revolutionary.”

What went down this week…

An Odd $100M – That’s the new amount of funding DraftKings announced this week. It’s a bit of an odd move, as many have pointed out, coming as the company is expected to merge with former rival FanDuel.

• The best reasoning behind this new funding comes from Dan Primackwho seems to know everything about DK, including the weekly lunch schedule and the password for the bathroom. You can check out Primack’s take at Axios, but his reasoning, that FanDuel is raising the same amount of funding as well and both rounds are meant to buffer the companies if for some time if anything goes sour with the proposed merger.

Madness – I’m convinced Rob May doesn’t sleep. The Talla CEO and local AI guru is at it again, leveraging Talla’s technology to help Slack users keep track of the NCAA brackets this year.

• All this is in addition to running the great AI newsletter, Technically Sentient and serving as a venture partner at Pillar. Methinks that the Talla Bracketbot pet project serves a dual purpose: Getting Talla’s great Slack capabilities out there to the general public, and allow May and co. work on something close to the heart with the hoops tourney. You see, May, originally from the Bluegrass State, is a hardcore Kentucky Wildcat fan. I wonder who he had going all the way this year?

Let’s Get Fired Up About Coverage – So Veracode is being acquired for a reported $600M by CA. While not in the stratosphere of the Dell/EMC deal, it is a major merger and a win for the Boston technology community. Other than some of the IPOs over the past few years, it is one of the largest liquidity events.

• And yet, The Boston Globe throws a sliver of coverage, from its device expert no less, at this news. And you’d be hard pressed to find other coverage out there about this as well. Veracode is one of the better homegrown startup stories, having been started inside the old Atlas Venture and led by Jeff Fagnan and Maria Cirino of .406 Ventures, who once served as Veracode’s CEO for a spell. (The image above is one that hangs up in Accomplice’s office and was included in a piece Fagnan wrote after the acquisition was announced…CEO Bob Brennan is in the middle with Cirino to the far left and Fagnan to the far right.) This isn’t the only news that has been neglected this week. There is news from Vaxess Technologies, Examity, NewStore, Digital Alloys, that just don’t seem to be important to some and yet could all be major employers in the area for years to come. Just saying…

Utterly not related, but a must read nonetheless

If you have some time, check out the profile of Jack White in The New Yorker: “Jack White’s Infinite Imagination.”

• The money quote: “Pushing myself into corners, identifying with the underdog, becoming the over-dog, being punished for that, retreating, advancing, learning to live in modern times, all the while creating at every turn. That’s the life path I chose long ago, and I couldn’t derail myself now if I wanted to.”

Utterly shameless self-promotion

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As I continue to build out the strategy for this thing, many have asked what the goal is. Well you know the scene at the end of “The Departed” when Marky Mark shows up and surprises smug, “I-got-away-with-it” Matt Damon. As I see it, Silicon Valley is Matt Damon and Boston is Wahlburg. So, I’m here so that everyone doesn’t end up too surprised when things flip.

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Screwed the pooch

There were some doozies last week.

The major mistake was splitting the credit and confusing two Harvard biz scholars. Clayton Christensen wrote the Innovator’s Dilemma, while Noam Wasserman wrote the Founder’s Dilemma. My B.

Also, here’s a link to the paper that features Nick Ducoff and Northeastern.