Part Two of the HelloParking postmortem: a look back, and a new perspective

Part Two of the HelloParking postmortem: a look back, and a new perspective

More than two years ago, Neil and I shut down HelloParking. We never managed to find product-market fit, and we were having trouble scaling. Before heading back to class and moving on, I wrote about our experience. In a rather long-winded essay, I exposed our triumphs, our failures, and told the story of HelloParking, a failed parking startup, to anyone who felt compelled to read it.

To my surprise, those who felt compelled numbered in the tens of thousands, and I’ve been contacted by many ever since publishing our story. As it turns out, we weren’t the only ones wanted to disrupt the parking industry. And as it turns out, where I thought we went wrong two years ago isn’t the full story.

After writing HelloParking’s postmortem, I’ve since moved on – I’ve learned about Lean Startups and Customer Development. I’ve ripened my understanding of how to shape products. And as all things on the internet have a tendency to do, my original post has lived on.  Because this one morsel of my past life continues to attract readership, I’ve decided it’s time to share an epilogue.

New insights:

To save the average reader from the toils of reading through the pages that follow, I’ve compiled my summary of new insights in the bullets below:

  • In the University of Entrepreneurship, Customer Development is a pre-requisite, and there’s no such thing as graduation. What you think you know is probably wrong. You can’t getting inside your customer’s head without getting out of the building. Any attitude otherwise is doomed to fail.
  • It’s not that the parking industry wasn’t ready for us. We weren’t ready, and didn’t know how to speak their language. 
  • Pivoting for pivoting’s sake is worthless. It should be a calculated affair, where changes to the business model are made, hypotheses are tested, and results are measured. Otherwise, you can’t learn anything.
  • When it comes to entrepreneurship education, nothing beats a good reading list and personal experience. Having graduated with a degree in Entrepreneurship, I thought I was ready to fire on all cylinders. I was wrong. Nothing has prepared me more for success in the startup world than a handful (a roomful, rather) of good books. Works by Steve Blank (Customer Development Guru), Eric Ries (Lean Startup Guru), and the Heath Brothers (Applied Psychology Gurus) are great places to start.
  • Ignore the hype. Focus on product-market fit, earlyvangelists, and bright spots. Along our journey, lots of really cool stuff happened. We got featured in the press (presspresspress, and more press). We were finalists in business showcases. We (nearly) made it to TechStars. I confused this excitement with success, and I should have seen it as a distraction.
  • Broadcast knowledge, and share failure. It opens doors and is helpful to others. Failure doesn’t need to be guarded, and shouldn’t be a source of embarrassment. Writing about what we learned attracted new connections and got me recruited into my current position, where I have been for two years.

“Why do you think you failed?” is a question I continue to get asked.

Years have passed, and with them I’ve grown a deeper understanding to the answer here. Our first model (“AirBnb for parking spaces”), has since sprouted dozens of fellow upstart imitations, without much success. Just like ours, many who started in this model have since graduated to the commercial parking space. It seems that the reason the AirBnb model hasn’t quite worked yet is the difficulty in collecting enough supply. Some have found marginal success at the hyper-local level, but none have found a model that works at scale.

More folks are hunting for parking spaces than exist parking space owners who are willing to share. This is the problem we weren’t able to solve, and a problem that still exists today for folks taking their own stab at the driveway sharing business. That’s not to say it’s a problem that can’t be solved, but rather it’s a tough one that has yet to be solved at scale (that I’ve seen, anyway).


And then we pivoted. And pivoted. And pivoted…

Our failed attempts at the “ZipCar for parking”, “Priceline for Parking” and “Groupon for parking” models followed in the months thereafter. And then we gave up. At the time, I was convinced that the industry wasn’t ready for our innovations. I was convinced that property managers and parking operators didn’t “get it” or just didn’t care.

That just can’t be the case. And it wasn’t.

I’m now the product manager at QuickPay, where I have been for two years. I know from first hand experience that parking operators are willing to innovate. They’re looking for ways to grow their businesses. But at the time, I just didn’t know how to speak their language. I didn’t know a lot of things. 


I did everything wrong.

First of all, I didn’t have a good understanding of the Customer Development model. And though I didn’t realize it at the time, doing “xyz for parking” isn’t the way to build product and discover value. The transitive property doesn’t apply as well in the startup world. (“If x worked for industry y, then x must work for industry z“)

The truth is, as co-founders of HelloParking we huddled together to decide on ideas that sounded nice, built prototypes, put on our salesman hats, and didn’t understand why we weren’t closing deals. And then we rinsed and repeated. We pivoted because pivoting seemed like the right thing to do.

But we never defined clear hypotheses, developed experiments, and we rarely had meaningful conversations with our target end-users. And while we had some wonderful advisors in the parking industry, we should have met with everyone we could get our hands on. Worst, we rarely got out of the building.

But at the end of the day, I’m fortunate to have had the opportunity to learn from my mistakes in my early twenties. And I’m fortunate to have been given a second chance as an early employee at QuickPay. I’m better for the experience, and have learned from it. I only hope that some of you out there can learn from my mistakes as well.


Share Button

Chris Hoogewerff

Product manager @Raizlabs. Enthusiastic about building products that influence positive behavior change. Energized by outdoor adventure.

More Posts

Follow Me:
TwitterLinkedInGoogle Plus

Thanks for reading! Subscribe here to get new posts sent to your inbox. Get in touch if you'd like to connect! I'm also on LinkedIn, Twitter and Google+


    • Jeremy,

      Thanks for the heads up! I found that the feature had been disabled by default on my theme. It’s back up now.
      Cheers, and thanks for reading.

  1. Hello Chris! Nice to meet you. Actually, really nice! We are developing the same project like your original one: “An Airbnb for parking spaces”. It’s called Parkinghood and we will start in Barcelona. Your 2 articles were a huge learning for me! Thank you very much for sharing.

    Actually, it seems that I’m following your steps because some months ago the responsible of another project, more focused in parking lots, asked for my collaboration. He is the owner of a parking lot and knows a lot about the industry (he speaks their language), so helping him I’m also learning a lot. As you know, when you try things, other opportunities will appear on the way.

    Right now, we are in the early stage of both projects. I know the Airbnb model will be hard (after reading your articles, I know it even more) but I don’t give up yet. I know about Lean Startup and Customer Development and I hope these tools will help me go further. If not, I will write an article and go for another project! ;)

    BTW I liked a lot the iniative of “Startup Obituaries” (I knew about you because of it).

    Keep in touch and good luck with QuickPay!

  2. Hello, Chris!
    I got to know about you from this article on a startup related blog.

    I am leading a startup in Moscow, Russia, that’s very close to yours and I would like to share my story for you and your readers.

    My background is in business processes analytics, logistics and production, so I used the lean principles and customer service activities a while before starting my project. So to start with customer behavior studies was quite natural to me. Though, as many of startup guys we (my partner and I) were always willing to give up CusDev and do the product.

    We started with an idea of, to be short, an Airbnb for stuff – a peer to peer sharing platform for things like baby gear, tourist and automotive stuff. And I still think that the idea is great. After a month of chaotic actions of CusDev we applied for an AlfaCamp2015, which is an eight week program to raise startups held by one of the leading banks of Russia – Alfa-Bank. They provide an office, bank and external advisers, Microsoft free tools and clouds, VISA and an internet initiatives development fund experts (no money though). We were chosen for the Camp with other 29 teams out of 850 that applied. We called our project Share EveryTHINK, so that we could add whatever sharing categories to our platform.

    After two weeks of CusDev “in the field” we understood that there was no market for sharing things in Russia, especially in automotive segment. But we got an insight from car owners we talked to about their parking pain. In Moscow there is a huge demand on cheaper parking. Moreover, there are 40% of car owners that are ready to pay more just for the opportunity to park in the center.

    The problem was we were very much concentrated on buyers, and forgot to check the sellers.

    Our other insight later was that Moscow is the city where almost nobody has an own parking place, so there is no legal way to lend (there are offline illegal solutions). And, as you wrote in your other post “those who have parking spaces guard them with their lives”. So we targeted the organizations that manage houses with yards and may share them for parking of cars of clerks that work close. Again CusDev and more CusDev…. and we gave up that idea because of no supply.

    Now we target the organizations that have parking lots in the center and we do even more CusDev. And we already have one that’s able and willing to lend a 70 spaces parking lot in the very center of the city. The Moscow government helped us – they raised tariffs for 50% from this month.

    Chris, don’t write that you did everything wrong. I bet you appreciate all of positive and negative experience you had. And I very much appreciate that you shared your story with us.

    For those, who read this, feel free to contact me for the sake of sharing thoughts and insights via facebook, the main of which is: never start doing a product before you can bet $100 that you know the answer a random person will give you to your question about your product.


  1. From beginning to end, the story of a failed parking startup - Chris Hoogewerff - […] shared some new insight in a more recent post: The HelloParking postmortem Part Two: a look back, and a …
  2. Part Two of a failed parking startup’s postmortem: a new perspective | Rocketboom - […] Part Two of a failed parking startup’s postmortem: a new perspective Source: 0    […]
  3. [101] ‘만약에’ 51개의 스타트업이 이야기하는 실패 요인 분석 (51 Startup Failure Post-Mortems) | Under the Radar - […] 헬로우파킹(HelloParking) 사후 분석 파트 II: 회상 그리고 새로운 관점 Title: Part Two of the HelloParking postmortem: a look back, …
  4. 51 Startup Failure Post-Mortems - […] Title: Part Two of the HelloParking postmortem: a look back, and a new perspective […]
  5. Parking Start-up failure: lessons learned | Innovation in action - […] See on […]
  6. Parcheggio, ecco le startup che fanno risparmiare tempo e soldi - […] di una piattaforma come la sua. Ciò dovrebbe bastare a vincere quella diffidenza che affondò Helloparking, esperimento americano che …
  7. 30 Founders Share Why Their Startups Failed - […] 15. HelloParking […]
  8. Actionable advice from 10 Uber for X start-ups that failed - - […]    HelloParking: Unable to find product market fit […]
  9. Nedlagda startups | Svensk internet business - […] Part Two of the HelloParking postmortem: a look back, and a new perspective […]
  10. 30 fundadores comparten por qué sus emprendimientos fallaron | Alfredo Atanacio - […] HelloParking […]
  11. 135 Startup Failure Post-Mortems | Qatar IT Forum - […] Title: Part Two of the HelloParking postmortem: a look back, and a new perspective […]

Submit a Comment

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <strike> <strong>

More in Product & entrepreneurship
Ask yourself every day: “What would it take to convince me I’m wrong?”

I recently came acro...