#BossBitch: Apparently being CRO means you get to ride in a $260,000 car

... now that's an ROI I can stand behind (er, ride in?)

Here's how it happened (and contrary to what everyone thought, it wasn't because of the Tinder race car driver):

Three hours after putting up the last post declaring that I wanted to drive a fast car, I got hit up by my buddy Matt confirming our evening ... we had planned to play trivia, but much to my surprise, he had something else in mind: 

I told him I was going the Live Planet demo happy hour, but would be free after that. 

Text you when I'm en route, he said. 

Done, I typed back. 

<tangent> Matt is co-host of a podcast with famed "car guy" Adam Carolla, and because of the popularity of their show, car manufacturers will often send them vehicles to review. He and I first met on twitter? (I think), and we've stayed friends over the years. About a month back he happened to reach out on twitter (not knowing that I was involved in a new auto/insurtech startup), and I was all dude, we need to catch up! So we did, and now that you're caught up, we can get back to our story ... </tangent>

That's Matt on the right.&nbsp;

That's Matt on the right. 

I got to the Live Planet event at the Roosevelt shortly after six, and was SUPER pumped to finally meet my buddy Chaim IRL.

We've known each other for at least six years, (as we're in the same digital social circle) but had yet to meet up face2face. 

CHAIM, I said super excited as we embraced. So great to finally meet!! 

JEN, he said, I'm so happy you made it. 

Thank you, I said. Are the demos still going on? 

Yeah, one is going on right now. 

Never one to be shy in going after something I want, I walked over to the small group and sat down directly across from Halsey (who true to form was still demoing)

<tanget> Chaim was in town because of Live Planet, Halsey Minor's latest VR project. Minor is an OG in the tech space responsible for CNET, and a few other tech ventures you might have heard of. (click here to read more) </tangent> 

I sat and listened (to what I learned was a very private partnership conversation), as I got a notification that Matt was going to arrive at 7:41. 

After the demo, Halsey and the group dispersed, as we all walked over to the "mingling" section talking to the rest of attendees. 

Chaim turned and asked, "what are you going to do now that Talk Nerdy sold?" 

"I'm Chief Revenue Officer of a new auto/insurtech startup called, DropIn (a full service on-demand live streaming platform), I'm in various stages of development with three new reality shows, and after that I'm going to play with animals." 

"What kind of animals," asked Halsey?

I'm not sure yet. I've always been drawn to dogs, but growing up I had a family of ducks, so who knows. All I do know is that if I put the intention out there, it will manifest (and manifest WAY better than I could have imagined). I grew up wanting to be a vet, and animals are the only part of my "career" that I have yet to fulfill. 

I then showed the group my phone which has this loverly photo ... 

... as I looked down noticing the time, 7:40. 

Shit, I said to Chaim, I have to go! I really wasn't kidding when I had mentioned that I am getting picked up in a Lamborghini. (I casually mentioned that I couldn't stay long moments into the event.) 

I hugged Chaim, ghosting the rest of the party, and as I ran out the door, I heard him say "Jen had to run, her Lamborghini is waiting." 

I laughed as I continued to run down the ramp and up the stairs outside. 

Matt had texted that he would be on the Orange side (street right by Roosevelt), and as I waited by the sidewalk, I saw a lambo in the distance. 

Not sure if that was Matt, I waited patiently for a text or call. 

I then see a wave from the vehicle. 

Oh, I said, that is you! 

I laughed running to the vehicle hugging Matt and saying, "only in LA do you have to wonder if that Lamborghini is yours or someone else's." 

I then swung my DropIn tote around asking if I could put it in the somewhere. 

Not a problem, Matt said attempting to open the trunk. 

Maybe it has to be in park? he asked. 

Don't look at me, I said laughing. 

He then figured it out, and grabbed my tote placing it snuggly in the trunk. 

My teeny tiny tote took up the whole trunk. HILARIOUS! 

Friel's station wagon: 1 Lamborghini: 0

Matt then fired up the engine, as I took a photo of my chucks commemorating this awesome life moment ...  


Where should we go, he asked? 

I'm at your mercy, I said laughing, I just can't believe we're riding around in a Lamborghini. 

Why don't we drive up the PCH and get some sushi in Malibu. 

DONE, I said hoping he didn't mean Nobu. 

We pull onto Hollywood Blvd, and everyone is (obviously) staring. 

Look at how low we were next to the Escalade. Wait, scratch that ... WE WERE LOW NEXT TO A MINI COOPER!!!&nbsp;

Look at how low we were next to the Escalade. Wait, scratch that ... WE WERE LOW NEXT TO A MINI COOPER!!! 

I then asked what all of the tech components were, as Matt gave a rundown. 

The second button from the left up top lifts the car front up and down so you can pull into driveways etc, and not scratch the car.&nbsp;

The second button from the left up top lifts the car front up and down so you can pull into driveways etc, and not scratch the car. 

He then pointed to the steering wheel which had three words: 

... and began explaining each one.

"Strada is for comfort (street driving), Sport is for fun street driving (90:10 Rear/Front AWD baseline), and Corsa for the track, it's super stiff and has the fastest throttle response, and shifting (60:40 AWD baseline)." 

We then hung a left down La Brea, and passed a G Wagon with the two gentlemen negotiating that partnership at the event. (They were admiring the ride.) 

HA, I said laughing.

Matt then hung a right onto Sunset and asked if I was ready to open her up. 

My response was simple ... 

Vroom! #lamborghini #notevenfullthrottle #sunset #tuesday

A video posted by Jen Friel (@talknerdytomelover) on

Friel's station wagon: 1 Lamborghini: 100

I then asked Matt how much a car like this cost. 

"This exact vehicle, he said, goes for $260,000."

Wow, I said realizing that this car costs more than the house I grew up in.  


I continued, I don't get it though, cars depreciate in value the second you take them off the lot. Why would anyone in their right mind spend this kind of money knowing it's going down the drain? 

It's not, he corrected. Depending upon the year, and specific models, these can actually be an investment; I've known people who have made millions off of vehicles like this. 

Wow, I said, still not fully grasping the business model but elated to have such a candid conversation with someone who knew their shit. 

An hour later, we arrived onto the Pacific Coast Highway (which pretty much was made for a moment like this)

Matt then FULLY opened up the car as I couldn't believe how smooth everything felt. 

It feels like we're riding on rails - I cannot BELIEVE it!  

I know, he said, it's incredible. 



Moments later, he pulled over.


Your turn, he said. 

No, no, no, I said super serious. I'm methodical, and I'm studying all of the components ... I'm a grandma ... I can't drive something like this. 

"You are the YES girl, and of all the moments you really need to say yes to this." 

AH, I said scared but getting out of the vehicle. 

I then sat in the drivers seat (the car still running), and said "but what about your insurance? You were trusted with this vehicle. This is a HUGE responsibility and I'm not taking this lightly." 

"I cannot believe you are thinking about my insurance in a moment like this, he said laughing. You'll be just fine, listen to the directions and enjoy." 

Okay, I said scared. I then went to adjust the seat (I am only 5'7 but all legs and very little torso -car seats have to be pretty far back for me to be able to drive.), as Matt corrected me. 

"You want your arm to be at a 45 degree angle, and lean back. It's not like driving a regular car, so it's going to feel weird at first." 

Woah, I said in the key of Fat Joe. You really do have to lean back. 

I then pulled off the side of the road, and fortunately there weren't a lot of other cars around. 

I'm going so fast, I said and I'm barely opening it up. 

Now, he said, let's put it in manual. 

No, no, no, I said content to stay in safe mode.  

"I can't get over you saying that word, that's not the Jen I know, he said putting it in manual. Use the left paddle (there's no stick) to shift down and the right paddle to shift up."

There's seven gears, I said. I've never seen that before. 

Without skipping a beat he said, "there's a lot you've never seen in this car before." 

After about 15 minutes, I decided I had tested fate enough, and asked where I could pull over. 

Let's just go straight to the sushi restaurant, he said it's right around the corner. </dreamsequence>

Moments later, I woke up from my epic nap ... 

... as we arrived at a strip mall (not Nobu thankfully). 

As we dined on some deliciousness, Matt and I finally got a chance to catch up. 

"I really admire you, he said. What you do is really hard, and to have kept it up for so many years is impressive."

Thank you, I said. That means a lot coming from you. I just love what I do, no one handed this to me, I created it. It hasn't ever been easy, but what in life is. 

Matt then drove us back to reality, as I laughed saying, "this car isn't my style, but I am definitely now getting used to being in it. DEFINITELY never thought I would say that!" 

"You're used to sitting in a $260,000 Lamborghini? That's the most LA thing I've ever heard, he said laughing." 

We arrived at my place shortly later as I gave Matt a big hug thanking him for a truly AWESOME adventure. 

Of course, he said. 

The next day, I packed my backpack ready to head to Chicago. 

<tangent> I had been contacted through Instagram by a photographer involved with the Fiesta Movement, asking if I could model for him at a classic car show.

See, I have been waiting to figure out the right time and "narrative" (if you will) to announce DropIn, and what a cool way to be able to do it!

Getting your picture taken while having people naturally ask "why is Jen at a car show" is WAY better than posting a simple LinkedIn update. (THERE IS ALWAYS A METHOD TO THIS MADNESS.)

I told him all I would need is a flight out, a hotel, and transportation to and from the airport.

Not a problem, he messaged back. </tangent> 

I arrived at the airport on time, and about an hour into waiting, I hear on the loudspeaker that all flights have been delayed due to a nationwide outage. 

Well, I said to myself, apparently there is someone in this airport that I need to meet.  

I then walked over to the bar to get some food, waiting for the next announcement. 

As I sat down, I struck up a conversation with the gentleman next to me asking him where he was traveling to. 

Vegas, he said. 

Oh man, I said, bet you wish you were driving there at this point. 

No, he said, I'm actually flying to Connecticut; Vegas is my connection. 

What part of Connecticut, I asked? 

West Hartford, he said. 

Hi, I'm Jen, I said outstretching my hand. Apparently I'm supposed to meet you, because West Hartford is my hometown. 

We then shot the shit, and three hours later, he excused himself to go and check the monitors. 

Do you mind watching my stuff, he asked? 

"Yes, I said. I'm going to steal everything in your bag and make the slowest getaway ever, I said laughing."

Moments later he came back saying, isn't your flight going to Chicago? 

Yes, I said. 

You're boarding right now. 

I then bolted like a banshee, saying please add me in social, and thanks for looking out! 

Because of the TREMENDOUS crowding, it was virtually impossible to hear anything. I assumed they would go back on the loud speaker, but they didn't (or maybe they did and now the loud speaker is more of a soft speaker); my new friend saved the day. 

As I got settled into my seat on the plane, I let my photographer friend know that I was late, but now finally boarding. 

I then fired up my laptop excited to watch some TV and zone out. 

Much to my surprise, I spotted some familiar faces ... 

Butch and Rooster!!!

Butch and Rooster!!!

I laughed realizing I hadn't caught up on the latest episode, but was excited to now. 

<tangent> I was on the West Texas Investors Club season 1, and I consider Rooster, Butch, and Gil family. Really fucking great people. Read more here. WTIC airs Tuesday nights at 10 on CNBC. </tangent> 

Little did I know the episode would also feature another friend, Manuel.

When I landed, I posted this on his Facebook page ... 

I then met up with my photographer friend, after quite the journey.

You must be exhausted, he said.

No, I replied, I stay pretty chill. As long as I have my computer, phone, and chargers I can make the most out of anything. 

We then discussed the agenda for the shoot as we arrived at the hotel. 

I'm so happy you're here, he said. I wasn't going to message you at first, but I know you say yes to most things, so figured why not give it a shot. I loved those black and white photographs you took. 

That was all Nick, I said. He's an INCREDIBLE photographer, but thank YOU so much for having me. 

I was so surprised you asked for so little, he said referring to the ticket, hotel, and transportation. 

"We're on the same road, I explained. I've been waiting for a cool way to announce my new startup (dropininc.com), and it's coincidental that it happens to be in automotive. You had perfect timing! Had it been for any other vertical or truly any other anything, I would have had to decline due to being so busy."

You're all over the place, he said. 

I laughed saying, "in more ways than one." 

As I went up to my room, I then unpacked all of the clothes from the shoot and laughed realizing I didn't bring any "normal" clothes. I was only there for 36 hours, but I literally didn't bring a change of clothing to leave in; I only brought what I needed for the shoot. (Which considering the alternative, it's not THAT bad, but traveling home in 50s pin up wasn't something I was looking forward to.) 

Oh Friel ... 

The next morning, I arrived on set, and laughed to myself realizing how normal all of this has become.

Here I am ...
on a Thursday ...
SOMEWHERE in the midwest ... 
hanging out on a set ...
with a photographer I met off Instagram. 

Regardless of the situation, I immediately found myself at ease. Everyone was professional, and the cars were BEAUTIFUL. 

The guys were hilarious. They were watching the shoot taking pictures, and in between models I said "if you guys want my picture, I want yours!!" Tit for tat, bitches.&nbsp;

The guys were hilarious. They were watching the shoot taking pictures, and in between models I said "if you guys want my picture, I want yours!!" Tit for tat, bitches. 

As I changed outfits, I laughed to one of the girls saying, "I feel like I need to be opening ovens." The wardrobe, hair and makeup are so foreign to me - yet I love it. I don't consider myself domestic at all, but maybe I can change my tune. 

Or not ... 

All of the girls were great. Not only beautiful, but smart, and all from all walks of life. One was a singer featured on American Idol, the other a nurse, and another studied genetics. 

Have you seen the Fergie M.I.L.F video? I asked. 

No, said one of the models. 

I feel like we're recreating that video:

Hours, and multiple wardrobe changes later, we left to head over to the actual car show (the Palos Heights Classic Car show)

<tangent> I had previously posted in social that I would be in Chicago, and my Facebook buddy Ray said that he would love to meet up. We agreed to meet up the night before, but because my flight was SO delayed, it didn't work out. Fortunately, with his work schedule, he was able to at least make the car show. </tangent> 

Ray and I finally found each other in the crowd, and I asked if he would mind if I live streamed us touring the cars. 

"Not a problem, he said. I'm honored to be part of your inaugural Facebook live stream." 

(I had mentioned that even though I live streamed almost a decade ago on both LiveVideo and Ustream, I had yet to use the Facebook platform.) 

We then went live, which bee tee dubs, is not as easy as it looks. 

See, the key to success on my LV channel was that I talked to everyone. Anytime someone came into the room, I made sure to say hi and thank them for coming in. A lot of other people on the site did their own "shows" of various sorts, but mine was always more of a conversation. I knew just as much about them, as they were learning about me.

I LOVED it, but this wasn't that. I did those shows mostly from my computer in my apartment ... this is on uneven terrain surrounded by hundreds of people, and shiny cars. 

Thankfully, Ray was a huge help (even bringing a Chicago t-shirt as a gift), and it felt great going live again after such a long hiatus. 

Ray and I then found a quiet bar to sit in as we were finally able to shoot the shit. 

Thank you so much for your years of support, I said sipping my wine. 

"Of course, he said. You're so interesting because you're beautiful, smart, and I can never guess what you're going to do next."

It's not me, I said, I got lucky that because of couch surfing and dating, I have friends all over the world that invite me to do cool shit. I then follow my heart and do the things that interest me.

I had NO idea that this week I would end up in a Lamborghini, but that happened, and I was happy. 

"These are the moments that I love though. Actually getting to talk to people and learning about their lives. Because I've published so much of my own people instantly open up, and I cut out the bullshit."

"It's great, he said. You're one hell of a storyteller."

Thank you, I said. 

We then wrapped up at the car show, and Ray dropped me back off on set. 

Thanks for coming out, I said. This really meant a lot to me. 

Thank YOU, he said as we hugged. 

Don't be a stranger, I said with a smile hopping out of his Jeep. 

I then took my new Chicago shirt, pairing it with overalls and pulled up a chair with the now growing group of people gathered in the garage. (It had started to storm so shooting stopped, and we all started to chill.) 

I smiled thinking back to the island life remembering how much I miss sitting around in a folding chair inside a garage drinking and shooting the shit with friends (old and new)

I then looked down and saw that I had a text from the Tinder Race Car Driver. (He and I went out on a date a few nights before.) 

N.I.L.F. ... M.I.L.F. ... at this point the lines were Robin Thicke style blurred.

A few hours later, we wrapped on set, as I bid adieu to the girls and guys retiring back to my hotel. 

The next morning as I got dropped off at the airport, I said goodbye to my new friend thanking him for the opportunity.

Absolutely, he said. Come back next year if you have time. 

I'd love to, I said smiling. 

My flight this time was fortunately only delayed a few minutes, and somewhere around past the point of exhausted I face-planted on my couch.

Between the 106 degree heat index, and high energy of the last 36 hours .. my body was ready to throw in the towel. 

However many hours later, I woke up in a pool of my own drool to a text from my girlfriend Chelsie. 

<tangent> Chelsie is the girl I met waayyyyy back in the day on the Playboy Mansion shuttle, and it was her couch I crashed on during the cockroach infestation. Poor dear even saw my apartment completely infested as I needed a witness for trial. She's the matriarch of my OG LA family. </tangent> 

I laughed thinking, THANK GOD that episode didn't air on my flight. I embarrass myself enough as is, I didn't need help from CNBC.

I passed right back out, and the next morning, I hit up my friend Nick confirming our plans.

<tangent> Nick was one of the 103 dates in 9 months, and he and I have stayed friends over the years having random adventures here and there. </tangent> 

Yeah, he typed. Let's go to the Tesloop startup pool party, it's over on the bluff in Playa. 

Done, I texted back.  

We then agreed to meet up at his place first, as he wanted to show me his new VR headset. 

I've previously tried Oculus, and I have to admit I wasn't impressed. While I went in open minded, I also wasn't hopeful. 

Moments into Audioshield in the key of Queen's "we are the champions," I changed my tune. 


About a half hour of game play later, we grabbed an Uber heading over to the bluffs. I purposefully didn't do a lot of research on the startup, as I prefer to ask questions straight to the horse's mouth first. 

Who's the CEO, I asked? 

Rahul, Nick said. 

Shut.the.fuck.up. I said pulling out my phone. 

What? Do you know him? 

Yes!! I pulled up his Facebook page, and it does in fact list him as the CEO and Co-founder. I haven't seen him in YEARS!!!! 

(The tech world is really really really small and we've all stayed friends because of parties and social media.) 

We arrived at the house about twenty minutes later to a handful of girls swimming in the pool, but overall a pretty chill atmosphere. (This was not the almost orgies of previous posts.) 

One of the girls (who lived at the house) opened up a vintage Pinot Grigio in this really funky blue bottle. 

Hilarious, I was actually able to find it by searching "big blue pinot grigio bottle." 

We all took a sip and realized it tasted like shit.

We weren't sure if it's because it's from 2009 and maybe white wines don't age the same as red, or maybe it just tasted bad from the get go and this was more of a novelty. 

Let's make sangria, said one of my new friends. 

I then went into the kitchen offering to help, and as I hand muddled berries, she asked how long I had been in LA. 

10 years previously, gone for 2.5 on an island, and got back almost a year ago. 

What island? she asked. 

Islamorada, in the Florida Keys. 

NO WAY, she said, my ex-boyfriend lives there. 

I half believed her, half thought maybe she was thinking of another town. It's SUCH a small place ... the odds of bumping into someone in Los Angeles that even knows what it is outside of Bloodline (they film in Islamorada) are astronomical. 

We then took a selfie, and she sent it to him. 

He confirmed that he does in fact live in Islamorada, and we have a ton of mutual friends. 

Small fucking world, I said. 

They continued to text as I finished the sangria. 

"He thinks you're really pretty, btw. 

You should hit him up next time you're in town. He's AWESOME in bed."

I blushed as I said thank you (who knows, I might consider it)

We went back to the table, as the group shook up with new members. 

What's your Facebook, asked one of the girls?

I gave her my full name. 

OH! I can't believe you're friends with Scott! I love him. 

Remember the dude I bumped into at the "accidental gala"? That's Scott. 

I just saw him back in December, I admitted. 

Let's take a selfie and send it to him. 

I smiled for another photo as she outstretched her arm. 

Rahul came down moments later, and we embraced. 

I can't even remember how long it's been, I said. 

I remember, he quickly replied. "It was the night I introduced Deepak Chopra with a ukulele at the Clearstone Ventures Partners CEO summit."

WOW, I said. Great memory! I remember you gave me a ride home, and I was really grateful. You even gave me an Eddie Vedder CD - it was awesome. 

I then took a moment, and laughed thinking how many people forget meeting Deepak Chopra? (I bumped into him on the stairwell.) Did I also mention that that was the day I went skydiving? 

I fell from the sky and met a god AND SIX YEARS LATER FORGOT ABOUT IT. 

Sometime early-ish into the night, I put on my onesie and put myself to sleep.

Day to night drinking is not my thing. 

The next afternoon, I went shopping to get a dessert for the DAR BBQ.

<tangent> DAR stands for the Daughters of the American Revolution, and is an organization (almost like a sorority) that you can join if you are a direct descendent of a patriot that fought for the independence of our country. They promote historic preservation, education, and (obviously) patriotism. I heard all about it growing up from my grandmother (who was VERY proud that we are direct descendants of Roger Sherman, aka the only duderino to sign all four of the US' big docs) but finally bit the bullet and decided it was time to join.

I wasn't sure what to expect from this bbq, but much like anything in life, was willing and open to see what would happen. </tangent> 

Now, this BBQ wasn't just in "a" neighborhood ... it was in THE most sought after neighborhood in all of LA. 

Translation ... time to get fancy. 

Unsure of the "dress code" I opted to wear the dress I wore at the Hawaiian pub crawl a few months back: 

Sans the blue wig of course.&nbsp;

Sans the blue wig of course. 

I paired the dress with some SERIOUS bling (all family pieces, except for one) and Charles David wedges. 

I then purchased a fruit tart, and I don't know what possessed me to do this, but en route I stopped my car and decided to walk the rest of the way (approximately one mile).

As I proceeded to walk down 3rd street, holding my fruit tart, I laughed at how hilarious this must look to people driving by.

Why is this girl in a semi formal dress, diamonds, wedges, walking with some sort of cake? 

I don't know why I did it, but it felt good, made me smile, and I have a feeling people in LA have seen weirder things. 

The event was incredible. About an hour in, the host gave a speech, and as I looked around the room at the different ages, and faces - I smiled realizing I am finally ready to accept the responsibility of my family lineage.

It took me 31 years to be ready, but hey, better late than never. 

As she continued speaking, I began tearing up remembering my grandmother, and realizing how proud she would be in this exact moment; CENTURIES of my ancestors have been part of this organization, and now I am continuing that tradition in her honor. 

She was a pain in the ass, but she was OUR pain in the ass.&nbsp;

She was a pain in the ass, but she was OUR pain in the ass. 

As the tears began to flow more, I snapped myself out of it by saying, QUIT IT FRIEL! She's just introducing the band!! (There was a band, and they were awesome.) 

A handful of hours (and WAY too much food later), I said good bye to my new "sisters," and walked the mile back to my car. 

I thought back to the past week, and laughed at how strangely awesome this place is in life. I'm accepting the responsibility of my family name concurrently with accepting a new job title, and all the responsibility of a Chief Revenue Officer (for a company I did not start)

Much like previous challenges, I'm sure I am ...

going to be scared
going to doubt myself
going to wonder who in the hell in their right mind would put me in charge of anything ... 

but I feel like that's the best part. 

I know I know what I'm doing, I just don't know what any of it means yet. 

Time to go find out. 

thanks SO much for reading this insanely long post. If you're in the automotive or insurance industries, I would LOVE to talk to you.
Email: JenFriel at gmail dot com

- xoxo, J

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