Chad Wittman of Dolly

Launching in 2014, marketplace liquidity, and the future of delivery.

Chad Wittman is the co-founder and VP of Product & Operations at Dolly, an on-demand moving and furniture delivery marketplace. You can follow Chad on Twitter @ChadWittman


You co-founded Dolly in 2014. What was starting, building, and scaling a marketplace like back then, and how has it changed over time?

2014 was full of folks trying to figure out the next Uber for X. This was a bit of a blessing and a curse for everyone that was in the general space. Investors either hated or loved the pitches in this space, but thankfully most customers were clamoring for these types of solutions.

Without Uber coming first, none of the other gig economy companies would have had the success they had. Customers needed the mental model and trust in the general concept before they would trust a "regular person" to take on their "specialized" work requests. This made starting easier than I typically would expect. 

As for building and scaling, we had to invent a lot of our own solutions or find vendors that were not thinking about this deeply yet.

For background checks I remember Googling "top background check company" and Sterling came up. We scheduled a call and the amount of manual work required to run background checks was insane to me. They had some flavors of integrations, but they clearly weren't built for developers. 

Another challenge emerged with managing a flow of gig economy applicants all the way to activation. We found a small company called OnboardIQ and we were one of their larger customers.

This allowed us to work closely with their team to help them better understand our challenges, luckily this allowed for their product to move in a direction that greatly benefited us quickly. They would go on to build a pretty big company now called Fountain. 

So you had this blend of old archaic systems + new nimble startups thinking about solving for marketplaces. This is definitely the biggest change in the past 5 years when it comes to building and scaling a company in this space.

Maintaining a balance of supply and demand in a marketplace is vital to achieving liquidity. How did you figure out the right balance of supply & demand, and how was that measured?

The balance of supply & demand is very unique to each company. It really depends on the utilization of each side, in addition to the value that's being created in the marketplace.

A unit of supply in our world can maybe do 5 Dollys per day, a customer may only need 1 Dolly every 3 months. So you have an equation that supports say 5 Dollys * 90 days = 450:1 ratio between our drivers & our customers.

This is more of a hypothetical ceiling, you also need to look at the typical utilization rate of your supply and the peak demand.

For example, say you have a 1,000 helpers available in a market on a given day, that gives you a theoretical 1,000 * 5 = 5,000 units of supply for the day.

But if your peak demand is 5,000 units of demand all requesting work at 10am, you actually only have 1,000 units of supply capacity for your peak hour. You're 1/5th supplied, but it's not economical to 5x your supply to cover only 1 hour of demand. 

I'll stop the math, but my point here is that you have to look at a couple of key pieces of data for each marketplace: capacity, peak capacity, demand, peak demand, utilization rate, & some sort of error rate to help fix things when they don't go as planned. 

The way I like to think about liquidity is over a dimension of time.

How does low liquidity in a given market impact our performance? What does high liquidity unlock in a given market? Is supply or demand easier to acquire or retain? What about a new market in low liquidity? Where can we invest to prop up demand or supply to start unlocking the benefits of high liquidity? How can we accelerate that flywheel sooner? 

To answer your question more directly, we look at things like customer price, driver earnings, customer ratings, driver ratings, a few proprietary driver metrics that try to assess a high quality experience on our platform, booking-to-fulfilled time, and other metrics that may be tangential to these concepts. 

What do you consider to be Dolly's sustainable competitive advantage?

Competition in our space is a really interesting topic. For the most part, most of the startups are hardly competing against each other.

We're really competing against non-consumption, traditional logistics / delivery companies, and truck rental (like U-Haul). To best answer your question, we'd need to talk about competition in each vector. 

For non-consumption, it's about educating the market to our solution & converting them into our customers.

I like to think about this in Geoffrey Moore's Crossing the Chasm mental model. For the people on the more progressive side of consumer mindset, we just need to let them know we exist & to try us once.

Once you get the Dolly mental model in your head, you'll see the world differently and will naturally leverage our service as you need it in your life.

For the folks on the more conservative side of the consumer mindset, we need to make sure we've built a great service that addresses their concerns. That might be things like top notch insurance, partnerships, & guarantees. 

For traditional logistics & delivery companies, it's about offering a product & service they have a really hard time providing.

I'm a big fan of Clayton Christensen's Innovator's Dilemma framework and I think it's really applicable in this particular case.

Most businesses tend to look upstream with their product offering. Additionally, they're by definition anchored to their unique value proposition. In this case, that's having large delivery trucks that are optimized to do efficient milk-run routes.

The upside with this strategy is that they can drive down costs against their fleets and any idle time for their delivery network. The downside of this approach is that the actual time of delivery per destination is variable, for the customer this manifests itself in a "please be home between 12-5pm for your delivery".

As we know being customers ourselves, that experience sucks. What Dolly offers (and a gig economy marketplace in general) helps enable is a smaller unit of supply (predominantly pickup trucks for us) that allows us to offer a much more customer oriented experience.

We can flex capacity, we can run point-to-point, we can do milk-runs, we can fulfill orders with a dynamic supply base of vehicle types. So for us, that means offering an excellent customer focused experience that's on the customer's schedule, with maximum customer service, and an even cheaper price. 

For truck rental, it's about trading money for time. It's often going to be slightly cheaper to rent a truck and do it yourself, but you're going to have a lot more headaches and probably 3x the time.

For us, this is about demonstrating this value proposition and making the entire process seamless. Every step of the process that adds time or stress, makes us less compelling against truck rental. This drives product development as well as operations, both are key in delivering an exceptional experience.

I view Dolly's sustainable competitive advantage as being a consumer focused, technology forward company built around providing the best way to move a big bulky object from point a to point b.

It sounds pretty simple, and it actually kind of is. The hard part is executing against that vision and not getting trapped into our business' desires instead of our customers.

I'm convinced that this will be the way that people move big bulky objects and I'm hopeful that Dolly is the company is the one that wins the space.

Between the companies doing something similar, we're all racing to see who can get high liquidity nationwide first -- the winner (in theory) should be able to service retailers and people moving alike better than any company out there. 

Some people believe that remote work culture and automation will negatively affect the moving industry and its workers.

What are your thoughts on this and what do you think the future of moving and delivery will look like?

Well there's a very large conversation to be had about automation and its impact on society.

The Agricultural Revolution brought dramatic changes to humanity, yet more jobs were created to now handle this new wave of work. The Industrial Revolution brought further dramatic changes to humanity, again...more jobs were created working on improving & fixing the machines we built.

We're now in the early days of the Digital Revolution. Will history repeat itself? Is this time different? In general, I believe that these revolutions have brought more opportunity & meaningful improvements in the quality of life for humanity. This gives me optimism about the future as it relates to automation and jobs. 

As it specifically relates to the future of moving & delivery, I think there are a few interesting trends playing out.

First let's look at delivery. Delivery has exploded in growth, between the internet, ecommerce, and specifically Amazon... the way we think about access to physical goods has never been more accessible.

A friend of mine was hosting some friends for dinner the other night, they wanted to do a puzzle, ~60 mins later an Amazon delivery was on their porch with a puzzle. 10 years ago, that would have been nearly incomprehensible.

Until we spend more time deep into VR or perfect 3D printing, I don't see the delivery business slowing down anytime soon. 

As for the moving industry, I think we'll continue to see people flocking to cities. I think we'll see continued rising real estate costs, which will mean fewer homeowners -- more renters. This means more moving, less stuff to move, and smaller square footage for their homes. These trends bode well for anyone in the moving business. 

In the delivery business, we’re seeing the Amazon-ification of traditional retailers.

They’re starting to realize that their customers expect more from them, especially when it comes to delivery. Customers expect deliveries to happen quickly, on time, and done with professionalism. That’s something very hard to scale and something even Amazon is struggling with, but Amazon is relentless on improving it. It’s why we’re seeing them buy airplanes, fund companies that will help them with their logistics, and experiment with gig economy delivery models.

Automation is probably a bigger concern for workers here. Big bulky things will presumably one of the later stage jobs to be replaced, but I suspect consumers will simply leverage labor in a different way. An example of that would be a delivery provider dropping off your item and dispatching local labor to assist with actually getting it within your home.

The opportunity to drive down the price with an automated delivery fleet will outweigh the inconvenience of solving a more dynamic local labor supply. 


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Jonathon Barkl of AirGarage

Pivoting, aligning incentives, and the future of parking.

Jonathon Barkl is the co-founder and CEO of AirGarage, a managed marketplace for renting physical space, starting with parking lots. You can follow Jonathon on Twitter @jonathonbarkl.


Where did the initial idea for AirGarage come from?

We started the company because we were trying to find parking near our campus at Arizona State University. 

We were paying $1,000 a year to park on campus, but all these people were sitting there with driveways, so I thought why don't I just go rent a driveway from someone?

I went and knocked on ten peoples doors and said:

Can I park in your driveway? I'll pay you whatever you want

Eventually, I found this guy named Ari who said, sure, I don’t use my driveway and I don’t have a car so give me a hundred bucks for the year and you can park there anytime. 

A hundred dollars was a steal because the campus parking was a thousand dollars for the year.

I took him up on that offer and started bragging about it to all of my friends. I basically said:

Hey, I got this super close and cheap parking spot and, you guys are suckers for paying for the on-campus parking

Just through having those conversations more and more people started saying:

Well, I would love to do that too. I would totally rent someone’s driveway but I don't want to go knock on a bunch of random strangers doors to get the parking spot. 

From there, we built this peer-to-peer driveway rental platform where we went and knocked on everyone’s doors and got some homeowners to list their driveways. 

It was a really cool product and people liked it, the news loved to talk about it, and it made a little bit of money but at the end of the day, what we figured out was that in order to scale, we would need millions of driveways and on a 1 sale = 1 driveway basis, it just never would have made sense in terms of unit economics. 

That's why about a year ago, we pivoted to do what we do now, which is started looking at churches and businesses and saying how do we make one sale and get not just one parking spot, but you know fifty or a hundred parking spots in their parking lots. 

Through co-creating with these parking lot owners, churches, and businesses we figured out that they were open to the idea of selling parking spaces but it needed to be much more than a platform for connecting people and it needed to be fully managed on their behalf. 

We do what we call full-stack parking management where we do the advertising, collect the payments, do the enforcement, and handle the immobilization of the illegally parked vehicles.

We handle all the operations that are involved in taking a parking lot from being just a piece of asphalt with stripes on it to a full-fledged parking operation.

What does a general pitch to these businesses sound like? 

The general pitch is:

You have this asset that you know has monetary value, and you're not doing anything to monetize it, or if you are doing something to monetize it, it's a huge problem, because it's distracting you from running your business, so you should focus on what you do best and let someone else handle a parking lot on your behalf.

For a lot of parking lot owners, churches, and businesses, it’s like we're creating found revenue for them—it’s like anything is better than nothing.

There are also other benefits like helping them better enforce, whereas before, they didn't have an enforcement system, so, our system becomes the system of record for anyone that wants to park there whether they’re a visitor or someone paying to park there.

Also, they can now enforce against illegal parking whereas before they kind of had to guess who was who and who was parked illegally and who wasn’t.

Which side (demand/supply) is your priority now and why?

We’re focusing most of our energy on the supply side of the marketplace and the reason we’re doing this is because the demand pretty much exists already, parking is a known problem. 

By being able to focus our energy on the supply, we're able to really focus on growth. 

Right now, what we're focused on is getting as many parking lots on board as possible.

What winds up happening is we, being the sole operator of the parking lot, install signs saying, if you're a church visitor, you have free parking, if you're not a church visitor, here’s how you pay for parking.

Essentially, the parking lot becomes a billboard for AirGarage. If you’re driving down the lot and see a park with AirGarage sign, you just pull in, pay, and do everything from your phone.

The nice thing is that the parking lot effectively acquires the demand for us so we can focus on the supply. 

What does the competitive landscape look like? 

Generally speaking, we see three kinds of competitors.

The first type is other parking apps that everyone initially thinks of, such as SpotHero, Parkways, and Park Mobile, which have come out in the last ten years, where they're just a payment layer or reservation layer on top traditional parking infrastructure.

All they do is help you find parking lots that already exist, and then they take a cut as a payment processor from the traditional parking operator that they're working with.

That was innovative in 2008 when you couldn't pay for things with your credit card in a lot of places, but now, it's not that interesting or innovative.

These things could be replaced by something from Venmo. If you run city meters, you can just put your Venmo handle on the meter and say Venmo is $5.00, with their license plate attached, and that's the equivalent of what these parking apps do.

We, on the other hand, are focused on competing with the traditional operators, which is the second category.

These are the companies that come in and sign a contract with a lot owner, and they either stick someone there to man the lot during the hours of operation, or they install a parking machine or a parking gate.

There's a wide range of these parking operators that are small-time operations all around the country with just one or two guys that run a few parking lots, or there are massive national groups like SD Plus which is the one publicly listed parking company.

They range in size, obviously, but there's about 10,000 of them around the country. They're extremely fragmented, and each one is pretty localized, generally speaking, except for the really big players. They’re also manual, offline, and quite old school.

What we're doing is building the tools to automate and streamline the back-ends that these guys are handling, so that we can become the distributed, larger-scale parking operator and operate parking lots that are less lucrative or out of the way where these guys can't survive, because their fixed costs aren't justified.

The third group of competitors are companies that compete with us in terms of supply in adjacent markets, i.e. companies that are going after this real estate but not necessarily for parking purposes—which is more of a future issue.

Why is right now the perfect time for AirGarage to exist? 

I think there are a lot of trends that are culminating towards what we're building.

One of which is the giving economy and the sharing economy.

I don't traditionally think of us as a sharing economy company, but we are in the sense of taking an asset, better utilizing it, and sharing it with more than the traditional users. So, it's like taking something that was previously single tenant and single-use and turning into a many tenant and multi-use space.

Another trend is the transition to contractor roles on demand—that's something we're doing that supports our position and our operations in the way that we do enforcement in our parking lots.

If you're a driver and you use our app to find parking, you can join what's called the Space Force. If you join the Space Force, you just can scan other driver’s license plates and report violators to us to earn free parking credit.

Previously, the job would've required someone to basically be on full-time staff and drive around in circles to check license plates constantly. We've broken it down to the individual task-based basis where you can scan a singular license number, and we’ll pay you for that single license plate.

Overall, I think the really important thing is if you can take a physical system, and make it legible to a digital system you can unlock a lot of value. That’s what we’re trying to do. We ask ourselves, how do we keep these parking lots, improve their occupancy rates, and utilization?

By doing so, we can reduce transaction costs and open these spaces up for new users to use.

To reiterate, there are a few macro trends that are going into it that enabled us to do this.

But, I think one of the more important ones is that we figured out a way to break down and itemize the back-end operations in many ways. A lot of parking operators had to have full-time employees for things we’ve broken down and gotten to our users as a simple task by task things.

What do you envision AirGarage's competitive advantage(s) being? 

There's a lot of things that go into us being competitively advantaged over traditional parking operators, even just basic things that seem obvious to a tech company but are very non-obvious for traditional, old school operators.

For example, an old school operator will rent the parking lot from you for a flat rate every month, then they'll sign a lease with you and they'll pay you $3,000/month to operate your parking lot, and then they'll pay something like $4,000/month to actually operate the parking lot. So, then they wind up having this $7,000/month fixed cost that they have to recoup.

This means their incentives are misaligned with those of the parking lot owner because their goal is to minimize the amount of time that you use your parking lot, so they can maximize the number of drivers that are paying for parking and using their lots so that they can maximize their revenue.

This creates a terrible user experience for the supply side. And, in this business, all that matters is the supply—if you own the supply, then you own the marketplace.

This thesis carries over to why the other parking apps have failed—because they built something similar to what Uber was built on, Uber built a marketplace where if one driver turns off their app, they can be replaced just as easily with the next driver and the rider will never know the difference.

The thing that's not true about parking is that the supply of lots is not identical because customers have a preference between parking lots, depending on which one is located next to where they're trying to get to.

Parking apps have been focused on this control and direct the demand thesis, but what they found is that actually doesn't give them the leverage that they were hoping for, only the suppliers.

The suppliers, these old school operators, still basically control this entire parking market and this parking economy. And it's a mess, and that's why parking is still such a terrible thing and prices are obscure, the experience is just awful, it’s all because the suppliers control everything and they're old school.

Those are a couple of our competitive advantages.

Our incentives are aligned with our lot owners, and we therefore also have low fixed costs where we can take risks on parking lots that might not necessarily make a ton of money because we're not paying them a fixed lease.

We're only paying them a percent of whatever we're earning.

The final thing that we're focused on is how do we build tools for the suppliers and the people that own the supplies so that we can then open up that supply for people to commence on demand. Those are kind of the things that we think about that accumulate advantages over time.

Hopefully, in the future, we’ll have strong network effects. But at this early stage, those are not things that we can necessarily measure.

What does the legal & regulatory landscape look like for something like Airgarage?

The nice thing is right now we're doing something well-defined already. We're just doing it in a way that's more technologically advanced.

The traditional parking operators are doing pretty much the same thing that we do, where they make a deal with private owners and sell parking on their lot. Towing is defined, and the mobilization of vehicles is defined. It's not like Uber or Lyft where you're defining something new.

We're just reinventing how we think about traditional parking operators, and take them and ask, if you could just start from scratch, how would you design a parking operator, given the tools you have in the 21st century?

So, the nice thing is legally speaking, everything's pretty cut and dry in the parking market.

What would a world with autonomous vehicles and AirGarage look like?

 Around 30 percent of the average American city is dedicated to parking.

This space isn’t always efficiently used, it's just poorly allocated. There are eight parking spaces for every car in this country—that's ridiculous overbuilding, and it's because 1) there are so many parking lot owners, 2) people have private parking lots and 3) the spaces are inefficiently used.

So, what we're trying to do is take these spaces that have traditionally been single-use, single-tenant spaces and transform them. Once we transform them into multi-tenant, multi-use spaces, we can open them up for many drivers to come in and use.

When we start to think about the future after we’ve built out this giant portfolio of real estate in cities, we ask ourselves:

  • What are some other use cases to extract value, higher value from these spaces than just parking?

  • How can we support the delivery, charging, and logistics for autonomous vehicles in the future?

  • How can we start to support that the charging and logistics of the micro ability solutions, such as scooters and electric bikes?

  • How can we support the future of cloud kitchens that are gonna be popping up in cities closer and closer to where people want to be in with delivering networks being built out today?

  • How do we support things like on-demand warehousing for someone like Amazon? Because as they get faster shipping, they need more fulfillment centers closer to consumers.

So, really what we're trying do is basically open up this portfolio in real estate and make it available as a platform that other businesses and people can build on top of, so they we can make cities more dynamic and more fluent, so that you don't have to, if you're like Enterprise Car, share a zip car, you don't have to go around to individual business owners and make deals with them individually in order to basically park with the cars throughout the city, and change this contract every six months when you need to reallocate your expenses.

You'll just be able to tap into the AirGarage API and build on top of the real estate portfolio that we're already managing as a distributed property manager or produce parking lots and other intention real estate and be able to just build your business much more fluidly and much more quickly.

Our goal is that, in the same way, that Stripe has become this API for interacting with the legacy payment infrastructure, and Twilio has become this API for interacting with the legacy phone infrastructure.

AirGarage will become this API for interacting with the legacy real estate infrastructure in a city so that businesses can be built on top of the cities more easily.

What was the process of raising capital like for you? 

The process wasn’t an “overnight success”, it was more so a years in the making type of thing, we had been just refining the business model and working closely with our customers for a long time.

When we finally decided that the product and operations were in a good place, it was time to prove out the thesis that these parking lots exist, we can acquire them and manage them, and, like, the best way to do that is to go out there and do just that.

That's why we decided to raise the seed round. We started with trying to raise an angel round. It was a small round of about $250,000, and our goal was to find people that have direct experience operating a marketplace company that interacted with the offline world but were online businesses.

We were talking to people from companies like Omni, Uber, and Opendoor—the types of marketplaces where they were built with technology, but manipulate the atoms of the physical world.

That's what we're interested in because that's what we're doing. It's very different than building a SaaS company. Because of this, we were looking for mentorship and advisors and convinced them to join us, and don't get me wrong, we had a lot of investors tell us no, so it's not like it was easy.

But after they got on board, they started saying:

This is sounding good. You should probably raise more money, get more runaway, and bring more people on to the team to really expand faster

Mainly because a part of this business will be a land-grab business—whoever gets these parking lot owners online and makes money first will probably be the one they'll stick with in the long run.

If you take someone from making zero dollars a month to making $1,000 a month, they're not likely to switch to another operator for an extra $100 a month, because you made them. That was a big part of it.

Fundraising felt like we were not making any progress for a while. And then suddenly, you’re brazed around. It’s just really weird trying to interact with investors and get them to follow whatever schedule you need, play your cards right, and stuff like that.

We talked to several firms and wound up choosing to go with Floodgate because they had already bought into the vision that we were pitching them on before we had pitched them on it—they had seen the future that we were trying to build in their light and were excited about the way that we were unfolding it.


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Martin Permin of Pelion

Airbnb, the chicken-and-egg problem, and the future of mentorship.

Martin Permin is the co-founder and CEO of Pelion, a marketplace for talented individuals to receive mentorship in return for Income Sharing Agreements. You can follow Martin on Twitter @purrmin.


Prior to starting Pelion, you were the first employee at Hive and before that, you joined Airbnb right out of high school, that's impressive. What were some key takeaways from those experiences?

I generally think that most people overestimate how well experience transfers. Context matters a lot.

To some extent, I had to unlearn a lot of things when I joined Hive from Airbnb.

When I left Airbnb the company was already on an inevitable trajectory. Working on growth there was very forgiving. In contrast, Hive was fresh out of YC when I joined and had pivoted the week before demo day. Shifting to the more inquisitive selling style needed pre-product-market fit took time and wasn't easy.

A lot more experience transferred from Hive to Pelion. Particularly how to operate well with limited resources. Resource constraints can be empowering; they shrink the decision space to essentials. Being hyper-focused in roadmap decisions is one manifestation of this.

People often say they want to start companies but don't, how did you know that it was time to make the jump?

For starters, I was a bit burnt out and largely unemployable. My co-founder Holger was in the opposite position and was drowning in job offers. Both of us wanting to start this company, in spite of different opportunity costs, inspired confidence.

"Increasing the number of high leverage work years in talented people's careers is something we'd been thinking about for years"

On the Eric Ries/Keith Rabois Continuum of Startup Strategy™, we lean towards Rabois, so we wanted to start a company only once we had a strong non-consensus vision for how to solve a large, fragmented problem.

Working in a market with obvious demand is like taking the moving walkways on your way to the airport gate. Sure, you might make the flight by running next to the walkway, but your odds are better if you run on it. We want to make our flight.

One of the hardest problems that marketplace businesses face in the early days is solving the chicken-and-egg problem. Which side (supply/demand) is your priority right now and why?

This is our biggest challenge right now.

Every day, my inbox is full of users asking for help finding the perfect mentor or mentee. Since our supply is very non-homogenous, we often have to scramble. We're blessed with top-line growth, but missing the supply-demand balance means letting down users.

We navigate this problem by optimizing for match rate rather than user growth. We keep matches as our Northstar, and constantly re-evaluate where the bottleneck is.

Network businesses are often built on the backs of other networks. Airbnb on Craigslist, Facebook on colleges, LinkedIn on email, and so forth. Currently, it looks like our version of this is Twitter, but we're still experimenting.

Describe a typical mentor and mentee. For example, is a mentor a seasoned guy with 10+ years of experience or a successful peer around the same age?

We have high variance in our user profiles for both roles. Highly experienced professionals with 10+ years experience sign up to find a mentor, and recent college grads sign up to be mentors. It's too early to tell how much of this is

explained by the Dunning-Kruger Effect, but perhaps the less experienced mentors are valuable in some non-obvious way.

It does thus far look like more experienced mentors provide more value. Perhaps because they're better networked. However, I suspect that the career distance between mentor and mentee shouldn't be too large, as this creates an unworkable inferential gap.

Our user base definitely skews towards tech, though we're also growing in management consulting, and finance. Within tech, one interesting tidbit is that most users are technical.

What do you consider to be Pelion's MOAT (or sustainable competitive advantage)?

It's important to differentiate between moats and competitive advantages. All moats are competitive advantages, but not all competitive advantages are moats.

Moats are what makes it hard for new entrants to capture our market share; it would be dishonest for us to speak confidently of those quite yet. We do have a strong vision for where we can build moats if we successfully execute.

Network effects create flywheels that can be hard for competitors to keep up with. Of course, all network effects are not created equal. We've recently seen assumed winner-take-all markets split amongst multiple companies (e.g messaging).

We will need to supplement network effects with a strong reputation system and great matching. Differentiated inventory helps here too. Switching from Pelion to a competitor is more costly than switching from Lyft to Uber.

Handling ISAs is another area where we can escape competition. Since tools to handle this aren't yet commodified, we have to build in-house, providing another hurdle competitors have to cross. Handling more ISAs will let us improve our tools, which will let us handle more ISAs, and so forth. Of course, this is a double-edged sword.

In terms of competitive advantages, I'll speak to the founder level. We've spent the past 18 months talking to hundreds of people looking to develop their careers. I‘m confident that we have a better understanding of our target users’ needs than anyone else. We've also both had non-traditional career paths, thanks to wonderful mentors.

Mentorship has been around since human existence, yet, it's still hard to find a valuable mentor, why is that?

I'm glad you bring that up. I believe that the best way to build a billion-dollar company is to take an ancient human desire and remove steps (h/t Ev Williams).

Finding a mentor is hard on three levels:

  1. It's hard to identify who the right person to mentor you is

  2. It's hard to get in touch with that person

  3. It's hard to convince that person to invest serious effort in you

The third point is the hardest to solve. Mentorship is investing time in others, so it's costly for mentors. Mentors expect a return for taking a risk, whether in the form of social capital, better employees, recognition, or a financial instrument.

Since most mentors rely on warm intros to mitigate risk, mentees have a cold start problem. This is especially true for mentees further from opportunity.

Our marketplace lists potential mentors, and incentives them to take an extra look at mentees who reach out. The ISAs provide an easy way to formalize the exchange of value.

Why is right now the perfect time for Pelion?

I believe that most startup ideas work out over a long enough timescale.

Market timing is everything.

We're capitalizing on a few trends in consumer behavior:

Educational credentialism is increasingly being met with skepticism. Coding bootcamps, the Thiel Fellowship, and Triplebyte are manifestations of this. Further, technology makes experience less important to output. We have a 17 year old employee with the same output as someone with 17 years' experience.

Secondly, there's renewed focus on new coordination mechanisms. ISAs and crypto are both examples of this. I don't think society, on the whole, is getting more Hayekian, but I do think we're getting more comfortable turning social subtext into overt markets.

If I wanted to learn more about this space, what should I be reading and who should I be following on Twitter?

Following Pelion is, of course, your best option!

Julia Freeland Fisher also has a lot of interesting work on her blog at the Christensen Institute, though primarily focused on success in an academic setting.

Julie Zhuo recently had a good Twitter thread that describes mentorship very concisely.

In a corporate setting, I think what Alice Bentinck and Matt Clifford are doing with talent investing at Entrepreneur First is super interesting (full disclosure: EF is a Pelion investor).

First Round's mentorship program is also interesting. Whitnie Narcisse who runs it is a worthwhile follow. Here's a good writeup.

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