WEBVTT

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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

00:12:32.279 --> 00:12:34.340
her first venture. The one where she got that

00:12:34.340 --> 00:12:36.360
crisis call during the Sandberg talk years ago.

00:12:36.519 --> 00:12:37.740
The one that had just bought her second venture.

00:12:37.820 --> 00:12:40.840
Seriously, they bought Fusion too. Yes, which

00:12:40.840 --> 00:12:43.559
put her right back inside that same large organization

00:12:43.559 --> 00:12:46.440
again. But this time, this time, this time she

00:12:46.440 --> 00:12:50.000
wasn't being pushed out. She was brought in proudly

00:12:50.000 --> 00:12:53.779
leading their top tier AI powered vehicle inspection

00:12:53.779 --> 00:12:57.580
application, the exact role that leveraged everything

00:12:57.580 --> 00:13:00.080
she'd learned. Wow. So the timing was wrong all

00:13:00.080 --> 00:13:02.539
those years ago. Completely wrong then. But because

00:13:02.539 --> 00:13:05.139
she didn't just quit, because she recalibrated,

00:13:05.519 --> 00:13:08.080
used consulting to pivot, gained skills in AI

00:13:08.080 --> 00:13:10.940
and computer vision. she became the perfect fit

00:13:10.940 --> 00:13:17.059
years later. finally matched her evolved skill

00:13:17.059 --> 00:13:19.620
set. What a journey. From that stressful bowling

00:13:19.620 --> 00:13:22.539
alley, parking lot, car sale. To leading a flagship

00:13:22.539 --> 00:13:24.840
AI product inside the very company that once

00:13:24.840 --> 00:13:27.259
represented her biggest professional setback.

00:13:27.379 --> 00:13:29.580
It just hammers home that careers aren't ladders.

00:13:29.659 --> 00:13:31.960
They're roller coasters, right? Twists, turns,

00:13:32.240 --> 00:13:34.360
unexpected drops. Absolutely. And those closed

00:13:34.360 --> 00:13:36.679
doors, they weren't failures. They were necessary

00:13:36.679 --> 00:13:39.860
detours that ultimately opened up paths to way

00:13:39.860 --> 00:13:42.080
more interesting, complex work. Work she might

00:13:42.080 --> 00:13:44.539
never have found otherwise. Exactly. She ends

00:13:44.539 --> 00:13:48.120
with this really insightful point. It often takes

00:13:48.120 --> 00:13:51.240
time, distance from an event, to see the why,

00:13:51.779 --> 00:13:54.039
to understand how it fits into the bigger picture.

00:13:54.259 --> 00:13:56.039
Yeah, the first reaction when a door slams shut

00:13:56.039 --> 00:13:59.860
is usually fear, maybe panic, urgency. Right.

00:14:00.240 --> 00:14:03.340
But the real skill... The resilience is in taking

00:14:03.340 --> 00:14:05.620
that breath, stepping back, using a filter like

00:14:05.620 --> 00:14:08.259
that three -legged stool, and looking for the

00:14:08.259 --> 00:14:10.720
actual opportunity hidden inside the setback.

00:14:10.820 --> 00:14:13.139
It reminds me of that Amy Poehler quote about

00:14:13.139 --> 00:14:16.399
career drive. How careers are like MSG. Uh -huh,

00:14:16.500 --> 00:14:18.879
yeah. How does that go? She says, no matter how

00:14:18.879 --> 00:14:20.639
much of one you've had, you always want more.

00:14:20.759 --> 00:14:23.139
That relentless energy to find the next challenge.

00:14:23.200 --> 00:14:25.460
That fits perfectly. So maybe the final thought

00:14:25.460 --> 00:14:27.440
for you, the listener, is this. Take a second

00:14:27.440 --> 00:14:29.570
and reflect on your own momentum. right now.

00:14:29.830 --> 00:14:32.409
Yeah. Is there a decision you're making, maybe

00:14:32.409 --> 00:14:34.570
subconsciously, that's based purely on fear?

00:14:34.870 --> 00:14:37.110
Fear of losing ground, fear of missing out, fear

00:14:37.110 --> 00:14:40.590
of irrelevance, rather than based on those solid

00:14:40.590 --> 00:14:42.809
three -legged stool qualifications, you know?

00:14:43.110 --> 00:14:45.590
Is this a real opportunity? Is the timing right?

00:14:45.830 --> 00:14:48.049
Is the team right? Is the support sustainable?

00:14:48.250 --> 00:14:50.789
Maybe it's time to stop running on fumes, hit

00:14:50.789 --> 00:14:53.429
pause for a beat, and choose your next door strategically,

00:14:53.769 --> 00:14:54.490
not fearfully.
