3 Digital, Pandemic-Friendly Holiday Gifts and a Car-Sharing Startup Worth a Second Look

Always 'good' on paper, car-sharing is having another moment.


The silly season is here! (How the ffff is it Winter already??) Usually, I take the lazy man’s approach to holiday gifting and just hand out a sloppily hand-written note with a gift card from a place I like to shop at… But, how does that work in a pandemic?? Do you just send a link via email 🤔

Here’s 3 digital, pandemic-friendly gifts that I will be sending this year (and to whom):

  1. For the people I love, but can’t ever find the right words. Songfinch, offers a personalized song that is as amazing to give as receive. Seriously. Watch this. You select an artist, share your feelings and BOOM! You’re the holiday hero.

    Buy a song and Save $25 with promo code: SONGNORI

  2. For the friends that I miss getting drunk with. Cameo, a shoutout from your favorite celebrity. If you haven’t heard of Cameo (especially if you live in Chicago) shame on you. It’s the ultimate, “I forgot your birthday… but Gary Busey didn’t” gift! Prices range depending on who you buy a shoutout from, but it never disappoints!

    Great deals running thru Cyber Monday on cameo.com

  3. For the kids of the friends that I miss getting drunk with. EarlyBird, an app that lets friends and family collectively invest in your child’s financial future by gifting stocks 🤯 Seriously though, do people with kids actually want all the shit we buy their kids?? Nooooo. Please send money. Better yet, send $TSLA.

    The app goes live in the App Store next week, but if you join early your first $15 investment is FREE 👉 https://bit.ly/3l56fjK

(Obligatory Intro) Every week I write an email brief on a startup that I'm looking to invest in and if you dig it, you can all invest right along with me via equity crowdfunding (if you don't know what that is, click here).

If you like what you see here and haven’t already subscribed, please do 👇👇👇

Now that we’re done Xmas shopping, let’s take a look at the future of car-sharing.

Invest in Upshift here 👉 https://bit.ly/39dKqfu

Subscribe to my podcast 👉 https://spoti.fi/3kVHU0y

DM me on Twitter 🐦 @kitun with any questions!


Company Bio

Upshift removes all the friction from owning a car. Whenever you need to drive somewhere, Upshift will deliver a Toyota Prius or Ford Escape hybrid SUV to your doorstep within 30 minutes — always clean, with a full tank. When you’re done doing whatever you’re doing — just park it in a service zone (like a Lime Scooter) and you’re done. No more expensive garages or circling the block for street parking. Forget worrying about parking tickets, break-ins, or mysterious new dents. Also, Upshift provides maintenance, repairs and full coverage insurance.

How is this different from ZipCar or Getaround, you may ask. It’s pretty simple. Previous iterations of car-sharing simply attempted to solve for the obvious [I need a car] problem, whereas Upshift assumes if you need to get somewhere you already know your options; they aim to solve for the issues that make both public transit and car ownership a complete pain in the ass. Insurance, maintenance, parking, cleanliness, people fucking with your settings, and on and onnnn.

Meet the Founder

Watch my full interview with Upshift CEO Ezra Goldman here 👉 https://bit.ly/2KHXQWU

Ezra Goldman is the Co-founder and CEO of Upshift. Prior to this, Ezra cofounded a dockless bikeshare in 1999 and helped design a shared folding electric scooter at the MIT Media Lab with Piaggio in 2006 while doing his Master's in City Planning. He's consulted on innovation for HP and was managing director of a tech startup in Copenhagen, where he also was a PhD candidate studying why Danish people ride bicycles.

Have you ever met someone that has led a life so completely singularly focused on something that you didn't even know was a thing? That’s Ezra. He’s been studying, inventing and operating ride share models since 1999. From MIT to Google, Ezra is a very well respected figure in the space with an added area of expertise that seems highly pertinent to this venture; city planning. More on this in my Terms & Takeaways.


  • 230,855 lbs CO2 eliminated, 50% female & 50% minority team

  • 1,500+ accounts, waitlist to subscribe, 15X growth in MRR over 7 quarters

  • Proven unit economics: 94% paid subscriber retention, $157 CAC, $4,842 LTV

  • Creating a new $26B TAM in high density US cities alone

  • Raised $1.25M+ including MINI (BMW) & NerdWallet cofounder

  • $250K NRE from Ford: pilot connecting Escapes to our apps + intent to scale

Let’s not forget how incredibly ambitious Upshift’s goals are. But, that said, their approach is very simplified — something that I think plagued those that came before them. Why offer dozens (or hundreds) of car models when two will suffice for 80% of use cases? Why source cars from people not in the business of making cars? And, why make people go out of their way when all people want to do is find their way!? Upshift has opted to build relationships with Ford and Toyota to simplify your options and their operations. And, this is as much the result of lessons learned as it is a newfound willingness of major auto manufactures to capitulate. All of this speaks to the improved unit economics for Upshift, as well as the potential to completely control the user experience (something previous car-sharing options fail to do).

Market Opportunity

Car-sharing is the startup idea that just won’t die. It’s the ultimate “good on paper” idea. Outside of a house, purchasing a car is often the most expensive asset a person owns. And unlike real estate, cars decrease in value from the moment you buy them, making them somewhat of a curious investment.

So instead of buying a depreciating asset, why not use a car only when you need one?

It seems easy enough, but the number of companies that have tried and failed to make it in this space suggests that the economics are exceedingly difficult to figure out.

ZipCar originated the car-sharing idea when it was founded in 2000 (an eternity ago by startup standards). The company was successful, going public in 2011 only to be acquired by rental car company Avis two years later.

There have been several copycats since then. GetAround, the most well-funded of the current car-sharing startups, with more $500 million in investment, has had an up and down year. Bookings and revenue fell off at the beginning of the dynamic, but surged over the summer as road trips became the most popular form of travel.

Kyte is another relatively well-established car-sharing platform, and it offers the same home drop-off feature UpShift boasts about. Turo has raised nearly $500 million in funding for its car-sharing service.

That’s before mentioning Lyft and Uber, the ride-sharing apps who have made it their stated mission to eradicate car ownership. Lyft is already offering a car-sharing service in some cities, allowing customers to rent and drive a car for an extended period of time. And Uber has invested heavily in automated driving in the hopes that its fleet of self-driving cars will be so cheap to rent that all other forms of car ownership and rental will be obsolete.

Terms & Takeaway

Invest in Upshift here 👉 https://bit.ly/39dKqfu

Security Type: Crowd Safe
Valuation Cap: $8,000,000
Discount: 20%
Investment Goal: $1,070,000
Raised (as of publishing): $522,565
Minimum Investment: $100

Here's what I like: The founder is exactly who I’d hire if I were Ford or Toyota attempting to build a new car-sharing business. And, the fact that Ezra has a Master’s in City Planning is invaluable in this venture — it’s what sets Upshift apart. In so many ways, past car-sharing models seemed to just operate on this broad assumption that lots of people don’t want to own a car… rather than focus on WHY they don’t want to own a car.

I think of Tesla here. They make millions of the same car. All of them. Just differentiated with software. To me, this successful re-engineering of consumer behavior by Tesla signifies a shift in how many people value their vehicles.

And, that opens the door for Upshift to capitalize on Tesla’s tailwinds.

Here's what I don't love: The above stated is also a double-edged sword.

Society seems ready for this type of seismic change, right? I mean, I think so. But, that’s just it. I have to make a major assumption here — it’s mostly out of Upshift’s control and I don’t like that.

They can do literally everything right and the market can still just spit them out.

Who should invest and why: It’s a BFI [big fucking idea] with a beyond crazy addressable market. Yet, the valuation is still pretty reasonable with an $8m Value Cap (the 20% discount makes that even more attractive). Strategic partnerships with Ford and an investment from BMW suggests automakers are certainly open to finding new ways to compete. So, it’s very possible that Upshift becomes an acquisition target, if not a big-time, Getaround-sized potential IPO candidate — but, it’s going to take time. A lot of time. And money. So, if you’re shopping for a quick flip or something with a comparable pathway to ROI; Upshift is certainly not that. It’s an ambitious idea for an ambitious investor. However, if it becomes the Lime of car-sharing, this is going to be an epic exit for anyone getting in this early.

As always, investing in private companies is super high risk, anything can happen. So, don't invest money you can't afford to insulate your closets with... Upshift has a lot to like but they don’t fully control their own fate 🤑

Invest in Upshift here 👉 https://bit.ly/39dKqfu

DM me on Twitter 🐦 @kitun

Disclaimer: It goes without saying, but this information should not be constituted as financial advice, my investing opinions are my own and all diligence is the responsibility of each individual investor.