David Pickerell

David Pickerell is the co-founder and CEO of Para. Para is an application which helps gig drivers choose better trips, reduce downtime, and find the best opportunities more efficiently.

Before launching Para, David worked at Uber, where he set up Uber’s Las Vegas operation as a Lead Operations & Logistics Manager. During his tenure at Nauto, an AI-powered driver behaviour learning platform to predict and reduce high-risk events in the mobility ecosystem, David helped raise $159 million in investment from Greylock and Softbank. He is also an early-stage investor at Yes VC, which invests in the Pre-Seed and Seed stages.

David is a Hong Kong native and attended Harvard University for his Bachelor of Arts in Political Science and Government. He has also held the presidency of the Harvard China Forum.

David is passionate about empowering people with information to improve their lives.

Where did the idea for Para come from?

The short answer is it was a couple of weeks into the beginning of the CoVID-19 lockdowns.

My co-founder and I saw a lot of misinformation online about gig workers. For example, people were unsure at the time whether the government would include gig workers while paying unemployment benefits.

So we built a simple tool—scraped all the government websites, realizing that if users answered five or six questions, we could give them different options. So answer five questions that will inform how much each program paid you, and on what timeline.

What does your typical day look like, and how do you make it productive?

I’ll walk you through my typical work week.

For me, Mondays are dedicated to being open to deep work.

A typical Tuesday and part of Wednesday are packed with team meetings and juggling different tasks internal to Para. I attend to tasks external to Para on Wednesdays and Thursdays.

To cap off the workweek, I try to keep Fridays open for deep work.

Moreover, it’s not all streamlined. I have to balance a lot of things depending on the current needs of the company. This effectively means some weeks are more operations-heavy, business development-heavy, or product-heavy.

My responsibility for heading Para is to ensure that everyone knows what we’re working towards right now and how their part fits into the cohesive whole. If something acts as a chokepoint, I do whatever I can to unblock them from achieving their objectives.

Lastly, I always try to reserve a small amount of time each week to network with professionals in the industry, develop relationships, and more.

How do you bring ideas to life?

Take a step back and observe the significant shifts happening in an industry over a period of time.

When we launched our tool, we realized that such shifts happened in the industry from when I was at Uber—all caused by the CoVID-19 pandemic.

Before CoVID-19, the average Uber driver only drove on Uber. Sometimes 20% of them also drove on Lyft. However, no Uber or Lyft driver drove on DoorDash.

Moreover, the average driver worked on one-point-something applications. For example, if you were an Uber driver, you couldn’t drive Uber and Lyft. Additionally, you forcibly tried UberEats, DoorDash, and other apps.

We are now witnessing the average driver go from one-point-something to three-point-something applications. This is because they are currently juggling applications in a way they didn’t have to deal with before.

So if you take a step back, people are working on more applications. And in fact, it’s not just three, but probably twenty viable options for the average driver.

That’s where we came in, merging the two stories and saying, “What can we do to build a system that helps the driver manage all of their things in a straightforward experience that puts the driver in charge?”

A system considers their preferences to talk back to the options. This system allows drivers to get their work done while driving safely. I think that’s how we started working on what we have today.

What’s one trend that excites you?

It is the idea of empowering individuals. We’re starting to see more and more tools that give power, data or abilities into the hands of the individual.

I always say building Para isn’t rocket science. The ability to ingest multiple trips, allow drivers to set preferences, enable navigation, and stack on behalf of the driver is a technology that hasn’t yet been available to the individual worker.

I see a lot of companies building similar things—giving this technological ability to the end consumer. This helps reach a state of democratization of technical capability.

This excites me, and I hope to continue seeing it over the next few years.

What is one habit of yours that makes you more productive as an entrepreneur?

I ensure to attack the core of a problem. I picked up this habit on the advice of a successful entrepreneur friend. Although I learned this early on in my journey, I wish I could go back in time and tell this to myself once more.

Therefore, I invest in solving immediate problems. This is why I have never invested in any FinTech or InsurTech solutions focused on the gig economy.

The only way you’d be able to build a set of services targeted at gig workers—InsurTech products or FinTech products—is to start by solving the immediate problem for the worker.

How can they make more money with less friction? That’s how you build a successful platform to solve more of the other issues – by solving the immediate problems of gig workers.

I armed myself with this philosophy through my prior work experience.

Previously, I worked at Uber—at a headquarters running operations. While leaving Uber, I heard from a bunch of drivers who said, “Hey, I didn’t know how much money I was making.” They said, “I didn’t know insurance would cost this much.” “I didn’t know there’s depreciation on the car,” etc. That stuck with me because I had an Excel spreadsheet where I could plug in the driver ID and find out to the cent what the driver’s net earnings were.

Before Para, I worked at an early-stage VC fund and got pitched a lot of the gig economy-focused solutions I mentioned earlier. But I always had that philosophy from my time at Uber: nobody comes home from driving 12 hours or working a 12-hour shift and gets excited about an insurance product. They don’t!

What advice would you give your younger self?

Stop overthinking things and just do it!

You always want to think what you have is the perfect thing. You ask yourself questions like: “Is this the first time somebody has thought about this?” “Have I thought through the entire strategy?”

In the last couple of years, I have learned that you will never know the answer to everything. You just have to start doing it. This doesn’t mean you won’t be thoughtful. If you have an idea and care about your passion, just do it.

Another lesson I have learnt is that to do something well; you have to make sacrifices too. I have sacrificed all the small ideas and a lot of things because the sustained effort required is hard.

Tell us something that’s true that almost nobody agrees with you on.

It goes back to the philosophy I mentioned earlier—I believe in empowering individuals with information to improve their lives. Bots should represent gig workers and work for the betterment of their interests.

This approach is vital to ensure that the more extensive system hears each worker’s voice and considers individual preferences. The result is progress towards a “perfect” system.

Most people will agree, but I don’t think there’s enough happening.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

The advice I’ve always given to myself, and I remind myself, is to use my product—really focus on the product. The most significant breakthroughs we have ever had at the company came when we went and did the work.

It is this idea that I remind myself of. I have a recurring calendar event on which I test the product. This sounds simple. It’s also a piece of advice you always receive if you go online and listen to what people are saying. But there’s a reason why people tell this, and it wasn’t until I did it myself that I realized its importance. I have to remind myself to do it continually.

What is one strategy that has helped you grow your business?

Our company’s goal is to determine how we can help. I just call it dollars and pockets. So what can we do to put dollars in our users’ pockets?

People always talk about the idea of a product market fit.

We found ours after we had launched a couple of versions of the tool. The first versions we launched had a couple of thousand users on it over a few months. And that was great.

But when we launched one of our killer features, which we call trip transparency, we saw the number of users go from 2000 users to 270,000 users in the space of one month. It was one of the times when it just went crazy. We realized we had reached the point where we had a product that people wanted. But, crucially, it was when we had something people wanted. The difference was just a whole night and day experience.

After the one-month period in which we scaled from 2000 to 270,000 users, we didn’t spend even $1. It was a complete word of mouth. To this day, we have not spent more than a couple of thousand dollars on marketing.

Almost all of our growth has been word of mouth. When people ask how that works, it’s pretty simple. The dirty secret is we make drivers money. Because we make them money, they tell each other about it. And that is how we’ve grown.

What is one failure you had as an entrepreneur, and how did you overcome it?

The first major tool we tried to build was what I called “automatic earnings tracking.”

Essentially, if a gig worker drives on five platforms, at the end of the day, they have to open up five apps to add what they made. We built an app that could track all the earnings in one place. We thought that it was a product. We had a couple of thousand users on it. At a particular moment, we looked at the drivers’ earnings. We found a driver making 30-something dollars an hour—a top-quartile driver.

We asked Eric (the driver) if we could drive together for a week to see how he worked. We wanted to see how he used our app. My co-founder, me and Jimmy, our first employee, drove with Eric for a week. The four of us would walk into every restaurant to pick up and drop off the delivery. Eric also let me drive while juggling multiple applications.

We learned that our earnings tracker was a nice-to-have product but didn’t solve any significant problems. We also learned that the application’s predicting where to work was not helpful. The driver already knew where to work and at what time.

Many believe that we tell how the driver can make the most money by choosing between Uber, Lyft and Grubhub using different variables. That does make sense. But it’s tough to predict!

This approach is where we started with our ideas. We can use data and tell you right now whether you should drive for Uber in two hours, then drive for Lyft, and a couple of hours later drive for DoorDash.

We realized that that wasn’t the right thing to do for several reasons.

If you’re an experienced driver, you know you need to drive to the airport in the morning and deliver food during lunch. You don’t need us to tell you that.

Second, if Uber cannot predict their price, with trillions of rows of data, in that case, we won’t be able to predict the difference between Uber and Lyft to a meaningful enough effect that is better than the driver’s mental model.

We allow the drivers to plug in their DoorDash, Uber Eats, GrubHub, etc., and all the orders come into one central feed. We give them all the different information they need.

We have taken it one step further. We allow drivers to set up a filter to establish parameters. For example, reject anything below $5. Or reject offers below $2 per mile. You can also do that if you want to avoid delivering a specific outlet’s order. If any order from all platforms fails to meet your criteria, we automatically reject it for you.

What is one business idea that you’re willing to give away to our readers?

There is a business plan which I have been thinking about, which is about compliance.

The business plan is about making information easily accessible about letting people go in compliance with government regulations.

I hate to let people go at the company, but sometimes such harsh decisions are unavoidable. For example, each time we have gone to a law firm and drafted a new document for, say, New York, Florida, or California, the law firms have charged around $1000.

There are more and more companies going remote—just like Para. People work across many states. Moreover, each state has specific rules on how to let people go.

I thought of someone building a website that talks to businesses about how to let somebody go. If a company has to let somebody go in the United States, how can they do it compassionately, respect the employee’s rights, pay them correctly, and fill out the proper paperwork?

If someone sets this up, it will be a great side business. They can sell a PDF for $100.

What is the best $100 you recently spent? What and why?

I paid $100 bucks to buy my sister a skiing lift ticket.

It is a big one for me since I’ve had to sacrifice a lot of personal time in building the company. These relationships still matter to me. If I can spend money to have a good experience with friends or my family, it gives me happiness.

What is one piece of software or a web service that helps you be productive?

We use a tool called OneSignal. It’s a push notification management software.

I love it because not only does it perform push notifications, but it also does modular in-app messages. Moreover, it can also tie together text, push, to in-app notifications to customer journeys. Users can map all of this in one tool. It is quite beautiful. We have sent almost 900 million push notifications through their system!

What is the one book that you recommend our community should read and why?

I’ve never really had a favorite. But I can share some of the titles I liked reading recently. The Climb by Anatoli Boukreev, The Rise and Fall of the Dinosaurs by Steve Brusatte, The Lessons of History by Ariel Durant and Will Durant, and Mindhunter by John E. Douglas and Mark Olshaker.

I always opt for a book when I want to learn or seek guidance on whatever I am working on.
However, I also prefer reading to broaden my horizons and simply unwind.

I wish I could read more fiction since most of my reading is non-fiction. I love it whenever I get the chance to read, and it’s a matter of not doing enough!

What is your favorite quote?

Theodore Roosevelt’s “The Man in the Arena.”

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

Or the British poem I also resonate with the message of the poem “Dulce et Decorum Est” by Wilfred Owen.

The poem’s Latin title takes from an ode by the Roman poet Horace. It means “it is sweet and fitting.” This poem closes with “Pro patria mori,” which means “to die for one’s country.”

Key Learnings:

• Focus on the central problems while starting up to build a successful platform. Give utmost importance to your target audience’s immediate issue.
• Remember to take a step back and understand the shifts in the industry—where are things headed? These are keys to looking into the future.
• Accept product feedback directly from your users. More importantly, be your own product’s user. This helps to feel and not just “get” criticism.
• To succeed, you will need to sacrifice personal time. Make it a point to commit resources to have good experiences with friends and family.