$650K in Three Weeks: Josh Pigford on Raising Capital for Startups

by | Jul 1, 2021 | Business

There are a lot of options when determining the right method for raising capital for you and your business. While there is no “right” way to raise capital, as it is based on several factors and personal preferences, one thing that is certain: your business will not succeed without capital – so it is best to figure out your plan early. One of the main factors in your decision-making will be how much capital you need, so you will want to ask yourself the following questions: What is my timeline? How long can I operate my business before I need additional funds? And how much funding do I need to achieve my goals?  

Once you have answered these questions, your next step is determining which route you will take for raising capital. Josh Pigford, currently the founder Maybe and previously Baremetrics, provides his firsthand insight and experience with raising over $650K in three weeks with micro capital and over $800K through institutional capital. Before we get into Pigford’s story, let’s start with some high-level pros and cons of each of these approaches to raising capital.   

Institutional Capital: Venture Capital  


  • Compared to other ways of raising capital, you can raise the most through VC  
  • The firms are incentivized to help you succeed, so they also offer support   
  • Funding helps you stick to your set schedule for development and maintain a steady pace  


  • Preparing for meetings with potential investors is time-consuming  
  • Not every personality type loves to pitch themselves – or their idea – in front of investors who meet with numerous entrepreneurs and only choose to fund a handful of projects 
  • Your investors may push you to be more aggressive in your growth strategy than you are comfortable with  

Micro-Capital: Crowd Funding  


  • Unaccredited investors can participate   
  • The entry point is more approachable; minimum amount can be as low as $100  
  • Your ownership stake in your SaaS business remains unchanged  
  • You don’t have to dip into your savings or take on debt   
  • A crowd funding campaign can help you jumpstart your marketing efforts and get prospective customers excited about your new product. 


  • The amount of capital you will raise is likely to be less than from other methods   
  • Fees associated with this route can be quite high (up to 8%)  

Different Capital for Different Ventures: Baremetrics vs. Maybe  

Pigford has been building on the web for over 20 years. He started as a teenager and has been self-employed for the past 15 years. Pigford is a serial entrepreneur and has built over 50 businesses, the most well-known being Baremetrics, a SaaS analytics platform designed for Stripe.   

Out of the 50 businesses he started, Baremetrics is the one that took off the most. “It wasn’t my first business, but it was the first time that I raised capital and then successfully exited.”  

Institutional Capital - Baremetrics  

Pigford started Baremetrics in 2013 and started realizing that SaaS metrics were not as easy to come by as he would have thought unless you were keeping track in a spreadsheet yourself.   

Payment processors were starting to take off at the time and Stripe was the first payment processor that you could reliably pull data from. Pigford started using Stripe for his other SaaS companies and decided he should build something that integrated SaaS metrics and Stripe.   

Pigford knew that internally he needed SaaS analytics that would build off Stripe so he started talking to other founders to see if they would be interested in something universal.  

He built the very first version in about a month and had zero intention of doing anything with it. He needed it for his other businesses to grow, but he never intended to market the product. He threw the product out there and a few months later its revenue had surpassed the other projects he was working on so he pressed paused on his other efforts and began focusing solely on building out Baremetrics. It worked out well as Stripe was simultaneously gaining momentum and no one else had been building something substantial on top of their API like Baremetrics was.   

At the time, Stripe only had around 90 employees (now they are over a thousand) so they were excited that someone was building something like Baremetrics. According to Pigford they were extremely supportive and they did a lot to help promote Baremetrics in the early days. 

Raising Capital for Baremetrics  

During the summer of 2014 Pigford started to raise capital for Baremetrics. Patrick Collison, the CEO of Stripe, stayed in regular contact with Pigford as Collison continued to grow the company’s metrics. One day he decided to fly Pigford to Stripe’s headquarters, as he wanted to talk about Stripe investing in Baremetrics.  

Collison and his team were looking to encourage people to build various products on top of Stripe to support the developer ecosystem. They ended up putting together a fund through General Catalyst, one of their major investors. Stripe decided to invest $500K in Baremetrics and suggested a valuation cap of $10M.   

“In hindsight, it was pretty insane. I pitched to no one and I was not pursuing any kind of investments at the time and all of a sudden the CEO of Stripe is suggesting $500K.”  

Pigford noted that the stipulations were that he had to be exclusive to Stripe for a certain period and could not be supported by other payment platforms. He was grateful for the investment in Baremetrics, which at the time was making around $20K a month. They had revenue but certainly nothing to justify the $10M cap offered by Stripe.  In the end, Pigford was able to raise $800K for Baremetrics. The other $300K came a year and a half later once Baremetrics was in a position where the company desperately needed funding.   

“That is the dark side of funding. You raise $500K, then you do what anybody does who just raised money: start hiring. As you grow, you hire more people and soon your revenue doesn’t match how fast you are hiring. We raised the $500K from Baremetrics in mid-2014 and then realized by late 2015 that we only had a month left of cash in the bank,” said Pigford. “That is when I started to do massive investor pitching, trying to raise more money.”  

While Pigford didn’t love the idea of writing and pitching and found it unpleasant talking about himself, he was able to obtain a $200K investment from General Catalyst under the same terms.   

“They very well could have changed terms to direct the transaction in their favor, but they decided to keep them the same and threw in a couple hundred thousand more,” Pigford says. “Then, Bessemer Venture Partners came in and invested $100K, which was what pulled Baremetrics over the line to be profitable.”  

That is the rollercoaster of fundraising. Pigford mentioned that asking people for money is never comfortable, but he had to remind himself that Venture Capitalists are used to that kind of pitch. The VC’s he was working with were wanting to help him build. When Pigford was raising the $500K he felt he had nothing to lose. He was building this venture solo. Once he got to the point where he had dozens of employees and their families to support, he knew that his perspective had to shift. He had salaries to pay, so pitching was necessary to avoid a desperate situation financially.  

Micro Capital – Maybe 

Pigford sold Baremetrics for millions of dollars and entrepreneurs everywhere knew his name. Once he began developing Maybe, a SaaS for modern financial planning and investment management, people were coming out of the woodwork asking if they could invest.  Pigford’s experience raising capital for Maybe was completely different because he had major success under his belt. He had money from selling his company, and therefore, had the capital to start Maybe on his own, but he knew there was something special about involving people who wanted to invest in the company themselves.  

Raising Capital for Maybe 

Pigford wondered how he could continue to raise money without having to pitch to investors, so he started looking into crowd funding for startups. Maybe was technically still pre-seed, pre-revenue and pre-product and the business didn’t have anything to show for it except for a few mock-ups and a good idea. Pigford decided to run the campaign through Republic, a crowd funding site like Kickstarter but the process was going to take over six weeks and there was a lot of SEC filing to do. The fees associated were also substantial so he started looking for other alternatives that could bridge the gap. That is how he landed on a 506(c) through Angelist.  

Angelist manages everything for you and has a $8K flat fee, regardless of what you raise. This is an appealing route if you expect to have a successful raise. All you have to do is bring in the investors willing to invest $1K or more. For a one-stop investment shop, Angelist was the best bet and Pigford raised around $650K over the course of about three weeks.  

Once the approval process for Republic kicked in, Maybe started to see interest pouring in left and right. People were giving from $100 to $50K and were completely on board with Pigford’s vision for financial freedom. Pigford plans to see close to 2,000 investors invest in Maybe from this platform alone.  

“I do prefer the process of micro-capital because it seems we are democratizing personal finance. With Maybe, we want people to be in control of their personal finances versus having to pay some financial provider or advisor associated fees for financial transactions, so it makes sense that we would like to see an equal playing field for people to invest without having to jump through a bunch of hoops to get accredited.” Pigford mentioned that from an ethos perspective, this style of fundraising matched up with the core values of his company, Maybe.  

“Every time someone invests, even $100, it is still an incredible feeling. The fact that our company is resonating with people – there is a certain level of validation there. I love that there are people who believed in Maybe from the start and are excited to invest in it to see where it can go in the future.”  

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