EXPERIENCE 004
Swimming Alone
Swimming Alone
Swimming Alone
Founder & Operator, Lokal LLC · Sept 2019 – Jan 2021
Founder & Operator, Lokal LLC · Sept 2019 – Jan 2021
Founder & Operator, Lokal LLC · Sept 2019 – Jan 2021
Sometimes the market wants what you’re building badly enough to tell you what it would take to fund it. The harder problem isn’t demand. It’s finding the one person willing to build it with you.
Sometimes the market wants what you’re building badly enough to tell you what it would take to fund it. The harder problem isn’t demand. It’s finding the one person willing to build it with you.
Sometimes the market wants what you’re building badly enough to tell you what it would take to fund it. The harder problem isn’t demand. It’s finding the one person willing to build it with you.
While I was working at OpenCities, I kept running into the same detail over and over, in RFP after RFP, negotiation after negotiation, every time I trained a city’s staff on a new system. Integrating a city’s legacy software with the content-management platform they’d just bought was never included out of the box. It always cost extra, roughly $3,000 per integration, industry-wide, and there was no off-the-shelf way to solve it. The municipal CMS market itself was small, really just three or four vendors, with Granicus and CivicPlus holding most of it between them. I started wondering why nobody had built the missing piece: a set of plug-and-play integrations connecting the top thirty or fifty legacy systems that municipalities actually run to the APIs of those major CMS providers, sold as a bundle or à la carte.
So I scaffolded the idea and took it to UMKC’s E-Scholars program, a competitive accelerator I already had some connection to as a mentor. The application deadline had already passed and the cohort roster was set. I made the case anyway; nobody else was building this, and I had an exit thesis that wasn’t hypothetical. A company called My Sidewalk had built a pothole-reporting app, reached 419 municipal customers, and gotten acquired by CivicPlus for nearly $20 million to be folded into their platform. I wanted to run the same play with Lokal: get enough traction to be noticed, then field acquisition offers from the players who’d rather buy than build.
It worked well enough to get real traction. I reached verbal commitments from twelve municipalities willing to pilot the product, and had a series of conversations with general partners at venture funds who were direct about what it would take to get serious: lock in a technical cofounder, hit specific milestones, and they’d talk numbers. A couple of them put rough ranges on what a raise could look like once those conditions were met, ranges high enough to tell me the thesis itself wasn’t the problem. None of that was a term sheet. It was informed interest from people who evaluate this for a living, conditioned on a piece I didn’t yet have.
That piece was harder to find than I expected. Building it right meant a .NET developer, and I’d been leaning toward writing the core in F# specifically because it would perform better and hold up longer as better infrastructure came online. In 2020, .NET and F# developers were scarce, well paid, and risk-averse, not a profile inclined to walk away from stable work to join an unproven startup as a technical cofounder. I talked to more than twenty of them. The pattern was consistent: real interest, real respect for the idea, and no appetite for the risk.
That’s where Lokal stalled. It wasn’t because the market didn’t want it. The pilot conversations were real, and the fund conversations were serious enough to be specific about what it would take to move forward. It stalled because the one piece I couldn’t build myself, and couldn’t hire fast enough, was the thing the entire plan depended on. I didn’t find the cofounder in time, the fund conversations never had the chance to become anything more concrete, and the company never shipped.
I think about Lokal differently than I think about the things that worked. It’s tempting to tell a story like this only once it resolves, once the acquisition happens, once the round closes, and skip the version where it doesn’t. But the validation was real. The exit thesis was sound enough that people with actual capital took it seriously enough to name conditions and ranges. The gap wasn’t the idea, the timing, or the demand. It was a single, specific dependency I saw clearly and still couldn’t close in the window I had. That’s a different kind of lesson than the ones that end in a win: sometimes you can diagnose the market correctly, build the right thesis, and still lose to a constraint that has nothing to do with whether you were right.
I don’t know that there’s a clean takeaway from that, and I’d rather say so than manufacture one. What I do know is that I’d rather be someone who can point to the moment a good idea ran into a real wall than someone whose portfolio only contains stories that were guaranteed to end well from the start.
While I was working at OpenCities, I kept running into the same detail over and over, in RFP after RFP, negotiation after negotiation, every time I trained a city’s staff on a new system. Integrating a city’s legacy software with the content-management platform they’d just bought was never included out of the box. It always cost extra, roughly $3,000 per integration, industry-wide, and there was no off-the-shelf way to solve it. The municipal CMS market itself was small, really just three or four vendors, with Granicus and CivicPlus holding most of it between them. I started wondering why nobody had built the missing piece: a set of plug-and-play integrations connecting the top thirty or fifty legacy systems that municipalities actually run to the APIs of those major CMS providers, sold as a bundle or à la carte.
So I scaffolded the idea and took it to UMKC’s E-Scholars program, a competitive accelerator I already had some connection to as a mentor. The application deadline had already passed and the cohort roster was set. I made the case anyway; nobody else was building this, and I had an exit thesis that wasn’t hypothetical. A company called My Sidewalk had built a pothole-reporting app, reached 419 municipal customers, and gotten acquired by CivicPlus for nearly $20 million to be folded into their platform. I wanted to run the same play with Lokal: get enough traction to be noticed, then field acquisition offers from the players who’d rather buy than build.
It worked well enough to get real traction. I reached verbal commitments from twelve municipalities willing to pilot the product, and had a series of conversations with general partners at venture funds who were direct about what it would take to get serious: lock in a technical cofounder, hit specific milestones, and they’d talk numbers. A couple of them put rough ranges on what a raise could look like once those conditions were met, ranges high enough to tell me the thesis itself wasn’t the problem. None of that was a term sheet. It was informed interest from people who evaluate this for a living, conditioned on a piece I didn’t yet have.
That piece was harder to find than I expected. Building it right meant a .NET developer, and I’d been leaning toward writing the core in F# specifically because it would perform better and hold up longer as better infrastructure came online. In 2020, .NET and F# developers were scarce, well paid, and risk-averse, not a profile inclined to walk away from stable work to join an unproven startup as a technical cofounder. I talked to more than twenty of them. The pattern was consistent: real interest, real respect for the idea, and no appetite for the risk.
That’s where Lokal stalled. It wasn’t because the market didn’t want it. The pilot conversations were real, and the fund conversations were serious enough to be specific about what it would take to move forward. It stalled because the one piece I couldn’t build myself, and couldn’t hire fast enough, was the thing the entire plan depended on. I didn’t find the cofounder in time, the fund conversations never had the chance to become anything more concrete, and the company never shipped.
I think about Lokal differently than I think about the things that worked. It’s tempting to tell a story like this only once it resolves, once the acquisition happens, once the round closes, and skip the version where it doesn’t. But the validation was real. The exit thesis was sound enough that people with actual capital took it seriously enough to name conditions and ranges. The gap wasn’t the idea, the timing, or the demand. It was a single, specific dependency I saw clearly and still couldn’t close in the window I had. That’s a different kind of lesson than the ones that end in a win: sometimes you can diagnose the market correctly, build the right thesis, and still lose to a constraint that has nothing to do with whether you were right.
I don’t know that there’s a clean takeaway from that, and I’d rather say so than manufacture one. What I do know is that I’d rather be someone who can point to the moment a good idea ran into a real wall than someone whose portfolio only contains stories that were guaranteed to end well from the start.
While I was working at OpenCities, I kept running into the same detail over and over, in RFP after RFP, negotiation after negotiation, every time I trained a city’s staff on a new system. Integrating a city’s legacy software with the content-management platform they’d just bought was never included out of the box. It always cost extra, roughly $3,000 per integration, industry-wide, and there was no off-the-shelf way to solve it. The municipal CMS market itself was small, really just three or four vendors, with Granicus and CivicPlus holding most of it between them. I started wondering why nobody had built the missing piece: a set of plug-and-play integrations connecting the top thirty or fifty legacy systems that municipalities actually run to the APIs of those major CMS providers, sold as a bundle or à la carte.
So I scaffolded the idea and took it to UMKC’s E-Scholars program, a competitive accelerator I already had some connection to as a mentor. The application deadline had already passed and the cohort roster was set. I made the case anyway; nobody else was building this, and I had an exit thesis that wasn’t hypothetical. A company called My Sidewalk had built a pothole-reporting app, reached 419 municipal customers, and gotten acquired by CivicPlus for nearly $20 million to be folded into their platform. I wanted to run the same play with Lokal: get enough traction to be noticed, then field acquisition offers from the players who’d rather buy than build.
It worked well enough to get real traction. I reached verbal commitments from twelve municipalities willing to pilot the product, and had a series of conversations with general partners at venture funds who were direct about what it would take to get serious: lock in a technical cofounder, hit specific milestones, and they’d talk numbers. A couple of them put rough ranges on what a raise could look like once those conditions were met, ranges high enough to tell me the thesis itself wasn’t the problem. None of that was a term sheet. It was informed interest from people who evaluate this for a living, conditioned on a piece I didn’t yet have.
That piece was harder to find than I expected. Building it right meant a .NET developer, and I’d been leaning toward writing the core in F# specifically because it would perform better and hold up longer as better infrastructure came online. In 2020, .NET and F# developers were scarce, well paid, and risk-averse, not a profile inclined to walk away from stable work to join an unproven startup as a technical cofounder. I talked to more than twenty of them. The pattern was consistent: real interest, real respect for the idea, and no appetite for the risk.
That’s where Lokal stalled. It wasn’t because the market didn’t want it. The pilot conversations were real, and the fund conversations were serious enough to be specific about what it would take to move forward. It stalled because the one piece I couldn’t build myself, and couldn’t hire fast enough, was the thing the entire plan depended on. I didn’t find the cofounder in time, the fund conversations never had the chance to become anything more concrete, and the company never shipped.
I think about Lokal differently than I think about the things that worked. It’s tempting to tell a story like this only once it resolves, once the acquisition happens, once the round closes, and skip the version where it doesn’t. But the validation was real. The exit thesis was sound enough that people with actual capital took it seriously enough to name conditions and ranges. The gap wasn’t the idea, the timing, or the demand. It was a single, specific dependency I saw clearly and still couldn’t close in the window I had. That’s a different kind of lesson than the ones that end in a win: sometimes you can diagnose the market correctly, build the right thesis, and still lose to a constraint that has nothing to do with whether you were right.
I don’t know that there’s a clean takeaway from that, and I’d rather say so than manufacture one. What I do know is that I’d rather be someone who can point to the moment a good idea ran into a real wall than someone whose portfolio only contains stories that were guaranteed to end well from the start.