Latest / Chief in Tech Deep Dive Shortcast / Chief in Tech S1E7 - Leslie Vander Baan: From the Bench to the Boardroom

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Chief in Tech S1E7 - Leslie Vander Baan: From the Bench to the Boardroom · Chief in Tech Deep Dive Shortcast

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  Welcome to the deep dive. Today, we're really
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  digging into professional resilience. You know
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  how those high growth tech careers, they almost
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  never go in a straight line. That's right. We're
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  looking at one specific journey today. It's got
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  startups, corporate life, acquisitions, and yeah,
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  pretty decent dose of what felt like sudden career
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  ending doom at the time. Yeah, exactly. And what
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  we want to do is pull out the mindset, the sort
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  of operational thinking needed to navigate that,
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  not just survive it, but actually use those setbacks.
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  Use them as building blocks, really. We're trying
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  to pinpoint those moments where, you know, anxiety
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  got turned into action, profitable action, strategic
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  action. There's this philosophy running through
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  the whole story. It's simple, but kind of sums
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  it up. The good days bring you happiness. The
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  bad days give you experience. And we're trying
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  to figure out how you cash in on that experience.
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  Right. how you make it work for you. Because
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  often from the outside you see this like multi
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  -million dollar venture, but inside it can feel
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  like pure anxiety. The source material actually
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  uses this great Tina Fey quote. It captures that
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  tension perfectly. Something like, my ability
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  to turn good news into anxiety is rivaled only
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  by my ability to turn anxiety into chin acne.
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  Huh. Yeah, that nails it. Especially when success
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  depends so much on, you know, funding and corporate
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  buy -in. Totally. It sets the stage for these,
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  like, anxiety mazes we're about to walk through.
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  Okay, so let's start with that initial leap.
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  This person, she had that classic itch, right?
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  Restless in her day job. Yeah. Didn't just want
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  to work for a great company. She wanted to build
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  one. That entrepreneurial fire. Which naturally
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  led straight to needing capital. Money. And that's
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  where this, uh, surprisingly stressful little
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  story comes in. to get funds, she's selling her
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  own car. And she describes meeting the potential
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  buyer in this neutral spot, a bowling alley parking
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  lot of all places, because she was genuinely
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  worried about giving out her home address. Felt
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  unsafe. Wow. OK, so she's sitting there on the
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  curb, stressed out. Totally stressed, terrified
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  the guy's going to just drive off with her car.
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  And right there, that's the aha moment. Really?
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  How so? It just solidified the need for a better
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  way. A trusted C2C consumer to consumer platform,
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  specifically for cars. You know, like eBay or
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  Poshmark. But secure enough for high value stuff
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  like vehicles. Gotcha. So that sparks the venture.
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  And they launch with like intense prep. Oh yeah.
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  Meticulous. Legal. Check. Real estate check.
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  Recruiting. Ops manual. Check, check, check.
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  Ready for the big picture challenges of scaling
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  this thing nationally. But launching is always
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  different in reality, isn't it? There's always
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  something. Always something. After all that prep
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  for the huge stuff, the very first car they sell?
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  They realize they forgot the most basic tool
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  imaginable. Don't tell me. A screwdriver. No,
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  no, to change the license plate. Exactly, a simple
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  screwdriver. It's such a perfect little example.
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  You can prepare for the giant regulatory nightmare,
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  but miss the tiny operational detail right in
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  front of you. So the lesson is, prep isn't everything.
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  You just got to jump in sometimes. You got to
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  start. Absorb those little lessons, the micro
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  learnings, as they happen. OK, so the business
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  gets going. It scales fast. And then this Fortune
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  750 company takes notice. They acquire it. Well,
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  they absorb the venture. She ends up co -founding
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  the car buying operation within this huge publicly
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  traded company. Ah, so inside the beast, which
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  sounds stable, but you said it brought new pressures.
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  Huge pressure. She called it riding a speeding
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  train while simultaneously laying the track.
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  They were moving at startup speed, innovating,
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  but inside this massive corporate structure with
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  all its rules. Compliance reporting. All that
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  fun stuff. Exactly. Bootstrapping, essentially,
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  but under a public microscope. But it worked.
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  I mean, the results. Undeniable success. Within
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  just a year, 12 months, this internal group scaled
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  nationally. They became the engine behind some
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  of the country's biggest car search websites.
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  Wow. So everything's looking amazing, like a
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  huge win. Looks like it. until it wasn't. Yeah.
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  The success story hit a pretty abrupt wall. Okay,
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  what happened? So fast forward five years. She's
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  deep into running this operation. She's also
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  heavily pregnant with her second child. She's
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  at a conference in San Francisco. Actually looking
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  forward to Sheryl Sandberg's lean -in keynote.
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  Maybe get some inspiration, you know. And mid
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  lecture, her phone rings. Oh boy. Not good news,
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  I'm guessing. It's a parent company. The boards
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  decided they want to change a direction, which
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  basically means they need to start winding down
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  this incredibly successful, thriving business
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  she built. Wait, wind it down while she's listening
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  to a talk about leaning in. An irony is just
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  brutal. Right. Getting the message to effectively
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  get out while hearing how to push harder in.
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  So why? If it was so successful, why shut it
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  down? Was it losing money suddenly? No, that's
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  the fascinating part. Operationally, it was solid.
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  Profitable. The source suggests the real problem
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  was structural. It was about how they had to
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  report revenue. Ah, the accounting. Yeah, the
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  methods they were using. Totally fine for private
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  company, but they just didn't mesh with the really
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  rigid reporting requirements of the publicly
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  traded parent company. So organizational fit
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  basically killed a successful operation. Pretty
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  much. It always trumps operational success when
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  you report to a public board, doesn't it? Yeah.
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  Wow. OK, so that call triggers... Well, I can
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  only imagine an emotional crisis. A huge one.
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  She's six months pregnant, facing, as she put
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  it, impending business doom and impending diaper
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  duty. And she still has to go to some professional
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  dinner that night. Oh my god, just juggling that
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  massive weight. And the stress, it hit physically,
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  immediately. On the flight back home, she gets
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  incredibly sick. Symptoms like a heart attack,
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  just intense stress -induced illness. Jeez. That's
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  terrifying. Yeah, the person next to her, some
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  tech guy, was apparently horrified. It shows
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  you the real cost of running that hard when your
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  whole system is just flashing red lights. And
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  then she gets home to face this impossible task.
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  Totally impossible. Liquidate everything. And
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  somehow convince her team, the people who are
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  about to lose their jobs, to stay on and help
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  shut it all down. Well, she's getting closer
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  and closer to her due date. Right. She knew the
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  whole wind down process would take her right
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  up to nine months pregnant. Unbelievable pressure.
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  So what happens next? Does she just collapse?
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  Not externally, not right away. And this is where
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  that fear trap really kicks in. It's so relevant
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  for anyone, you know, facing a big professional
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  blow. How so? Well, she'd proven herself right.
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  People knew her work. Industry colleagues were
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  calling wanting to meet, discuss future roles.
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  OK, so opportunities were there. They were starting
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  to appear, but she just kept pushing, flying
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  across the country for meetings driven by this
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  fear stricken Anxiety, she called it. Terrified
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  of losing momentum. Running on fear. Totally.
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  Until her doctor basically had to step in and
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  say, you need to slow down or you're going to
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  have this baby in another state. Wow. A literal
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  wake up call. You mentioned her compass for decision
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  making was malfunctioning. What did that look
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  like practically? It meant she was just saying
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  yes to everything. Taking meetings, interviewing
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  for roles. But out of panic, not strategy. Reactive,
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  not proactive. Exactly. She realized she was
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  bombing these meetings because she was just running
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  on fumes, making choices purely based on fear,
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  fear of being unemployed, fear of becoming irrelevant,
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  instead of looking at it like, is this actually
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  a good opportunity? That immediate pressure to
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  just do something, anything, blinding her to
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  the need to do the right thing. Precisely. OK,
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  but wait. She's a successful executive taking
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  a full pause, stepping back. That feels like
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  career suicide sometimes, doesn't it? How did
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  she justify hitting pause? She reframed it. She
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  realized the pause wasn't stopping. It was recalibrating.
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  It was necessary. OK. So she deliberately stepped
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  back, started reading, listening to podcasts,
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  seeking inspiration. But critically, she also
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  got really clear on what she actually wanted
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  next. She built a framework. Ah, the three -legged
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  stool. This sounds important. It was her filter,
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  her way to fix that broken compass. For any future
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  entrepreneurial thing she'd consider, it had
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  to meet three specific criteria. No exceptions.
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  Okay, what are the three legs? Right. Number
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  one, the market timing had to be right. Is the
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  world ready for this idea now? Makes sense. Number
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  two, the dollars. Real funding. Enough to actually
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  support sustainable growth. Not just keep the
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  lights on for six months. Crucial. And number
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  three. The right team. The right people to partner
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  with. Skills, vision, temperament, the whole
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  package. Market, money, team. If any leg was
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  wobbly. The opportunity was out, instantly disqualified.
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  It gave her this objective way to evaluate things
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  instead of just reacting out of fear. Smart.
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  So armed with this new filter, she doesn't jump
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  into a permanent job. No. Instead, she makes
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  this really strategic pivot into short -term
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  consulting, even taking projects a bit outside
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  her usual wheelhouse. Consulting. After running
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  a national operation, did that feel like a step
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  down? You might think so, but it was actually
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  brilliant. She said she started networking like
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  it was her job. Ah, using it as intel gathering.
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  Exactly. Consulting let her expand her skills,
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  test the waters in different areas, meet potential
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  partners, see who was doing interesting things,
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  all without the long -term commitment. And it
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  gave her head space. Clarity. Huge clarity. She
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  actually realized that some of her best, most
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  innovative ideas came during those reflective
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  periods, not when she was in the thick of operating.
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  That's a really key point for anyone listening
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  who might be in a down cycle or pause. It's not
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  wasted time. Not at all. And she also realized
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  something else important. What's that? Her personal
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  brand was strong, really strong. Think about
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  it. She was getting job offers while nine months
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  pregnant and actively shutting down her last
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  business. Yeah, that says something. It says
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  people value your track record and your potential.
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  She realized, you know, you're constantly being
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  evaluated for roles that don't even exist yet
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  based on how you handle yourself, especially
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  through difficulty. So leverage that brand. Okay,
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  so the consulting and the three -legged stool,
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  how did that lead to the next big thing? Well,
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  that networking paid off. A contact from her
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  previous gig, the one that scaled really fast,
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  reached out, had an idea, a potential venture.
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  And she runs it through the checklist? Ran it
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  through the three -legged stool, right market
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  timing, check. sustainable funding, big check.
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  This one had serious backing. Oh yeah. Who's
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  involved? Some heavy hitters. Billionaire entrepreneurs,
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  actually. Eric Levkowski and Brad Kiwell, guys.
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  Known for huge successes like Groupon. Experts
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  in big data aggregation. Wow. Okay, so definitely
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  the right team, and dollars legs were solid.
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  Absolutely. She had successfully used that pause,
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  that reflection, to position herself for a partnership
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  with truly visionary, rock solid investors. She
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  joined them. OK, so she dives into this new,
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  well -funded venture. And this leads us to the
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  first full circle moment, which is honestly kind
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  of mind blowing. It really is. She works hard,
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  builds this new venture, makes it successful,
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  and then she leads the sale of that business.
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  Don't tell me. To the exact same Fortune 750
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  parent company. No way. The one that told her
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  to get out five years before. The very same one.
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  The structure, the timing. It was all wrong back
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  then. But now. She'd proven the concept's value
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  externally, built it successfully, and sold it
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  right back to them. An incredible validation.
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  That is incredible. Vindication almost. So after
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  that major win, what's next? Start another one.
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  She actually decided against starting from scratch
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  again. Her focus shifted. She wanted to partner
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  with really solid teams, visionary entrepreneurs.
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  immerse herself in the ecosystem. Wow. Investing,
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  mentoring, more strategic consulting. Her philosophy
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  became, discovery is always in the doing. Keep
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  engaging, keep learning. Okay, staying active.
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  And that doing led her to another key consulting
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  gig, this time with a company called Fusion,
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  really cutting edge Silicon Valley tech. What
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  were they doing? Applying 3D computer vision
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  to machine learning, specifically in the automotive
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  space. So it perfectly blended her deep auto
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  industry knowledge with this advanced AI tech.
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  Very cool. And I have a feeling this leads to
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  the second full circle. You guessed it. The story
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  doesn't stop there. Fusion, this innovative tech
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  company she's consulting for, gets acquired.
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  By? By the same company. The one that had acquired
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  her first venture. The one where she got that
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  crisis call during the Sandberg talk years ago.
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  The one that had just bought her second venture.
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  Seriously, they bought Fusion too. Yes, which
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  put her right back inside that same large organization
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  again. But this time, this time, this time she
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  wasn't being pushed out. She was brought in proudly
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  leading their top tier AI powered vehicle inspection
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  application, the exact role that leveraged everything
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  she'd learned. Wow. So the timing was wrong all
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  those years ago. Completely wrong then. But because
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  she didn't just quit, because she recalibrated,
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  used consulting to pivot, gained skills in AI
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  and computer vision. she became the perfect fit
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  years later. finally matched her evolved skill
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  set. What a journey. From that stressful bowling
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  alley, parking lot, car sale. To leading a flagship
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  AI product inside the very company that once
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  represented her biggest professional setback.
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  It just hammers home that careers aren't ladders.
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  They're roller coasters, right? Twists, turns,
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  unexpected drops. Absolutely. And those closed
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  doors, they weren't failures. They were necessary
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  detours that ultimately opened up paths to way
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  more interesting, complex work. Work she might
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  never have found otherwise. Exactly. She ends
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  with this really insightful point. It often takes
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  time, distance from an event, to see the why,
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  to understand how it fits into the bigger picture.
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  Yeah, the first reaction when a door slams shut
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  is usually fear, maybe panic, urgency. Right.
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  But the real skill... The resilience is in taking
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  that breath, stepping back, using a filter like
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  that three -legged stool, and looking for the
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  actual opportunity hidden inside the setback.
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  It reminds me of that Amy Poehler quote about
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  career drive. How careers are like MSG. Uh -huh,
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  yeah. How does that go? She says, no matter how
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  much of one you've had, you always want more.
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  That relentless energy to find the next challenge.
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  That fits perfectly. So maybe the final thought
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  for you, the listener, is this. Take a second
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  and reflect on your own momentum. right now.
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  Yeah. Is there a decision you're making, maybe
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  subconsciously, that's based purely on fear?
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  Fear of losing ground, fear of missing out, fear
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  of irrelevance, rather than based on those solid
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  three -legged stool qualifications, you know?
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  Is this a real opportunity? Is the timing right?
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  Is the team right? Is the support sustainable?
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  Maybe it's time to stop running on fumes, hit
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  pause for a beat, and choose your next door strategically,
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  not fearfully.