This is the completely unglamorous story of my startup I co-founded with my friend and business partner, Adam Bickford. A couple months ago it was acquired by our first investor who now manages it and is taking it in a new direction.

Usually you read about startups on sites like TechCrunch where a startup in San Francisco made some app that does something inane like sends “Yo” to your friends and raises million of dollars their seed round that later sells for 100s of millions to billions of dollars. You rarely hear about how truly fucking brutal it is. It’s not the long hours that most founders say in interviews, it’s the mental anguish. The euphoric Mt. Everest highs and depressing 6ft down under lows. That’s what I’m writing about today.

Brace yourself for this is a long read…
Names of partners have also been changed to faked names


The early days

It all started with an email to Adam. I told him I had an idea for an app and he told me to shoot him over my idea. If you’re curious, these are the original emails.

A week or so later we started wire-framing it out then started hacking away. Our initial prototype used MongoDB, Geddy, and Backbone. I forced myself not to design the prototype at all yet so I could focus on functionality.

This was literally our very first prototype “design”

Once we got the tech of the prototype functional I emailed a designer friend of mine who had kids also and pitched it to him. He loved the idea too and designed the app. Here was the very first comp made 3 years ago.

After that we just kept hammering away at it on the weekends and at night. We’d spend most of our Saturday or Sunday working on it. We’d meet either at one of our places or go to bars or coffeeshops and switch each week who was driving out to who. We did that for over a year.

In August 2014 we made an Angel.co account mostly for fun. We weren’t expecting anything legitimate from it but on the 21st of that same month we got an email from a local Portland investor, Jakob Knightly. He wrote to us through Angel.co and simply sent us:

good idea.

At the time I had no idea how to respond to an investor. I was scrambling. I did some googling then sent a way too long and detailed email back and waited a couple days. He asked to meet for lunch one day to see our prototype. We rushed through the prototype adding a bunch of completely faked out features like comments and practiced exactly how we’d go through the demo.

The last commit we made on the prototype before our meeting

We met with him for lunch and he seemed excited. Adam and I walked back to Adam’s car beyond excited. “We met with an investor and he liked our stuff. Holy shit, that happened”, we said.

A few days later he wrote to us asking if we could meet again. We met him at a pub in downtown Portland and asked us a few more questions. Right then and there he offered us a deal. He told us he’d give us $100,000 to take the prototype from prototype to functional beta. At the time we had a deal waiting to be signed with MoneyBiz™ (fake name to keep them anonymous, but the company is a Fortune 500) and our prototype was functional so this was totally doable.

Adam and I rushed to get an LLC setup, find a lawyer, and get everything in order for an investment. We got the paperwork handled and signed and met at Portland City Grill where we shook hands and he wrote us a check for $100,000 right there at the table. For us, he put the angel into angel investor. Here’s a picture of that day with my eyes closed looked like a doofus and my hair about half it’s current length.

The euphoric days

After the check I gave notice at Simple and left 2 weeks later to work full time on Piggybank. Adam left his job as well and we both started the same day at an office space called The Leftbank Project in Portland. It was like a dream. We were our own bosses working on our project making our own design and code choices.

That first week flew by. We redesigned the app in a few days to be more modern and rebuilt it in React. We figured the most obvious way to go about launching this thing was to build the software right the first time and when we go to show future investors they’ll ogle at it and throw money at our faces. So that’s what we did. We spent months building this app with no banking integration at all while we waited on our banking partner at the time, MoneyBiz™, to finish things up on their end.

We went sort of viral for awhile in Portland. We were interviewed by two TV stations, were on the front page of the Lifestyle section of The Oregonian and their blog, we had a radio interview with some station in Austin, as well as some other smaller blog interviews. Since Fox was one of the TV stations that interviewed us our interview was syndicated on all the other local Fox stations across the US. We were getting hundreds of beta invite signups a day.

At the same time this was going on we had launched a Kickstarter to raise some more money. We were planning on using this money to hire a backend engineer. We had a video produced with custom music, shirts, stickers, and everything made. We thought this would blow up with all our hype.

This was, unfortunately, the highest point. The honeymoon phase was over.

When the news spelled my and my company name wrong

The downward days

The first fall

While all this traction was a huge help for email sign ups to build up momentum once we launched this didn’t help our Kickstarter campaign at all. I had a friend at TechCrunch who had promised us a story when our Kickstarter launched and a lot of our estimations of how much we’d raise were based on that. This person didn’t write the article though. I sent email and Twitter DM after email and Twitter DM but never heard back.

Despite having nearly 1,000 people subscribed to our mailing list which we emailed multiple times, 95% of the people who funded our Kickstarter were friends and family not even part of the mailing list. As the hype ended in the media and without any word from TechCrunch we decided to pull the campaign and try it again later when our audience was bigger and we had a better plan.

This was extremely rough for us. This was our first real true failure, but we dusted it off and kept going. When we figured out we wouldn’t have money for a backend person I stopped working on design and front-end and went all to backend development getting ready for our MoneyBiz™ integration.

The $1 founders lunch of champions

The second fall

We signed an official contract with MoneyBiz™ the last day of December. We waited until the final day to make sure we could do it. These banking contracts leave you in debt of 100s of thousands if you don’t follow through with your launch dates or meet your minimums and last for years. Adam and I had beer, listened to metal, signed the contracts and sent them over. We had been talking to banks for months. Some of whom told us to, in essence, “get lost”. We had this specific contract sitting waiting for us to execute with MoneyBiz™ since September. This was about half a years worth of work, so this was a big, exciting, deal for us.

About halfway through January we get a call from our MoneyBiz™ person. He gave us some terrible news. They were going through some internal investigation or something. They couldn’t tell us much for legal reasons. He said you can stay with us but we wont even be able to begin working with you for 3 months minimum, but it could be much longer. For this reason he offered to void our contract and help us find another company.

We got intro’d to MoMonies® (another fake name) from our MoneyBiz™ contact right away. MoMonies® seemed like the perfect bet. We never heard of them before because they were a startup just breaking into the space that is mostly made up of just a handful of large companies. They were responsive and had an amazing, real-time API and were more willing to negotiate. We were starting all over again though and they told us they couldn’t launch until the summer, but they were guessing a “99%” chance (remember this number) we’d get approved by their banking partner.

This was a minor setback though. Things were finally starting to look up again. All we would need to do is go out and raise some more money, but this time we had to raise big money.

The up-again days

We pretty much stopped all product development and went full time into fundraising mode Q2 of 2015. While our Kickstarter was a flop we met another investor through it and he was willing to invest to keep us going until the end of the year to raise more money. We had help from a previous entrepreneur, Patrick Algrim, the founder of Digit.co, to mentor us on fundraising.

We worked our asses off networking for months. We pulled every string we could get our hands on and asked for intros to probably 50–75 people. We got meetings with roughly 15-20 VC firms. We flew to New York, San Francisco, and even drove to Bend, OR meeting with the some of the biggest firms out there. This was an incredible experience. Adam and I aren’t salesmen or business people, but having to do this jolted us into a business person perspective. We had to learn fast.

Part of this was applying at accelerators. We got denied repeatedly for all of them, except one: Y Combinator (YC). YC is the tech accelerator. They get thousands and thousands of applications and they only pick a small percentage of them to meet in person. We were one of them.

The waiting area before you get interviewed

This was huge. We practiced our pitch repeatedly. We had our answers down to a T. We flew down there for our interview and waited in their weird all orange room. I was beyond nervous. I was about to have an Eminem spaghetti moment when they called us in.

The interview went by in what now seems like a blip, but I remember nailing it. We came out thinking there was nothing we could have said or done better. We waited anxiously to see if we got in when we got the email.

We were not accepted.

Their reasoning was that while they loved us and the product and, as they said, we “answered everything perfectly”, we weren’t integrated with our bank partner so if they put us in their program there was a chance we’d be in and out of their program without ever launching or even being able to do any product stuff.

Little did we know that worry was dead on.

The when-it-rains-it-pours days

It was like a punch to the gut not getting accepted into YC and knowing you nailed everything you could have and being stuck because of your bank partnerships, but, again, we dusted it off and kept going. We had dozens of interested VC firms we were in talks with so we weren’t too worried yet.

With investors following our updates now we decided to ramp up marketing and get a bunch of new signups and use that as leverage before asking for money. Our first and only hire, Jessa Graves, did this exceptionally well. She brought us our best month ever with signups before we even had a product and with no current press happening. She turned nothing into something. We were showing significant month over month growth so we thought now or never on our raise. We started asking the month we have about 1,000 signups in 30 days.

We spent weeks going and meeting with investors again. Right in the middle of these talks, and literally while in San Francisco fundraising, we get a call from MoMonies® while we were in the TechCrunch office. They had some bad news. They told us their bank partner is not comfortable with our concept. They couldn’t work with us unless we had either real users with significant traction or millions in the bank (remember that 99% number I told you to keep in your mind? Yep).

The roof of the TechCrunch office on 410 Townsend

MoMonies® offered us hope though. They had another program where they partner with the bank and we are sort of a “sub” account. We couldn’t do custom cards and there was more restrictions, but we could at least launch a pilot program. Problem was, this program was still in the works and they didn’t know when it would be done.

This made the talks with the investors really, really tough. One by one we kept getting “you’re too early for us right now”. We got down to the bottom of the barrel and out of our $700,000 bare minimum needed, we only could raise less than $200,000.

Then the final stab to the heart came.

The end of days

We were at a little less than $200,000, but we had a couple of investors who still hadn’t replied and enough runway for a couple more months. We had a final strand of hope that we could get a lead to come in and fill in the rest or if we could just get a couple more $100,000 we could go leaner and make it work somehow with some sort of small product pivot.

But then the final blow came from MoMonies®. We had a call with them right after a call with one of those late responding investors. I was outside in the rare Portland sunshine. The call with that investor was one of the most optimistic we had heard in weeks. I was ecstatic and this call with MoMonies® was supposed to be a meaningless update. It wasn’t.

They told us their program was finished, but the bank wasn’t able to review it until next year sometime. This was in early October, so we’d be blowing our current investors money plus any new investments we took for potentially months just sitting around since our side of the product was done.

Adam and I were both completely broke. I maxed every credit card. I was paying part of our employees salary out of my savings. I was going to the bank and taking cash out and depositing it into our business account to pay salaries and expenses. My savings was down to basically a month of personal bills and thats it. We were behind on payroll taxes and lawyer fees we couldn’t afford.

Adam and I had what we saw as two choices:

  1. We could take the smaller investments, pay off these debts, and figure out some pivot and hope for the best
  2. Stop further payments from our current investors and hand over what we have so far and walk away

It was one of the hardest choices I ever made but we decided to go with option 2. We stopped the payments coming in from one of our current investor and we gave all ownership of the company and intellectual property to our first investor in trade for paying off all our company debt so we were free. He has an idea for a new direction that is bankless so we decided it was for the best.

We already felt terrible for not being able to launch or raise more money and to drag it into another year without any sort of promise of actual bank integration seemed selfish.

I felt defeated, and oddly, I felt lonely. You always hear about the successes of startups and never the failures unless they’re catastrophic so at the time I felt like I was the only one out there that failed even though I knew the stat that 9/10 startups fail in the first 2 years. Only a couple people know this but I had an actual mental breakdown one night sometime after all this happened. I didn’t even know those were real things until I had one. It was like going through a death in the family.

a before and after working in startups

Long live the Yorkshire Interactive days

When all else felt hopeless Adam and I decided to launch another company (because apparently we must be batshit). We launched Yorkshire Interactive a little over 6 months ago. We wanted to help other startups, especially ones who’ve never been through it, with tech and business consulting and contracting.

We started out modest. Our first month open we brought in only $3,200 (which meant only a $1,600 pay check for the whole month for each of us). However, we’ve been growing our total revenue at nearly 95% month over month while keeping our expenses at about about same and even increasing profit margin. We have a steady income again and the savings in our business account keeps growing. We’re finally no longer struggling with money and mentally I’m back to pre-Piggybank again.

We’re excited to see what Jakob does with Piggybank and we wish him the best in his new vision for it.


Here’s some things I’d like to tell entrepreneurs reading this:

  1. If you need to raise money to launch your product do that first. Don’t even think about building out your product outside of a very simplistic prototype. Once you have runway to build it from start to finish, then start. If you’re in the fintech space a contract alone isn’t enough. Make sure everything is set and done and ready for integration from the start. Absolutely none of the code or design matters if your partnerships don’t exist or you don’t have money to run it.
  2. Prepare yourself for serious emotional turmoil. Expect to not be able to sleep and when you do get yourself to sleep to then wake up in the middle of the night in sweat.
  3. It’ll get better even if you crash and burn. 6 months ago I thought all was lost. Now, however, Adam and I are more financially successful then we ever have been. Although we didn’t raise we built an incredible network that has been invaluable with our Yorkshire Interactive venture.

If you’re starting a company, thinking about starting one or in the middle of running one and would like to chat I’m always happy to talk with other founders and offer advice and feedback. You can tweet me or email me at oscar@yorkshireinteractive.com