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