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Bootstrapping to Exit, Then do a VC-Funded Venture: Cordial CEO Jeremy Swift (Part 5)

Posted on Sunday, Nov 21st 2021

Sramana Mitra: How did you get your first customer?

Jeremy Swift: By scratching, clawing, begging, and pleading. We had a pretty great wealth of relationships.

Sramana Mitra: That was my question. Did you go back to those relationships? When you have domain experience, you also have relationships in a category. It’s easier to sell into a category when you have those relationships.

Jeremy Swift: It is. I will tell you though. We specifically went to our relationships first. Some, we did have zero relationships with. They took a huge gamble on us. One was Daily Insight Group that’s just outside of Portland. They were one of our first customers. This channel is very critical to their business. They took an absolute flyer on us. You need those people who are willing to bet on you and believe in the entrepreneurial vision and spirit of what you have.

When you’re building off of these three to five-year financial plans, we thought that our relationships would just take this company to the moon in a heartbeat. Email was driving 20% to 45% of total revenue for an online business. You don’t just rip that out because you have a relationship with Jeremy. You need to have some conviction and maturity behind that business as well. That was always the push and pull. The relationships took us so far. We really had to prove our mettle with respect to technology and product to go alongside those relationships. 

Sramana Mitra: The disadvantage of going into an existing category is that there are exit barriers for products that are already entrenched. It takes work to dislodge those products and take their place. How did you do that?

Jeremy Swift: We incorporated our network and relationships into an ICP. This was such an interesting environment. You just feel like you’re up against the clock all the time. We had not raised venture at that point. I was perpetually out fundraising for the first two and a half years the company was living off of seed capital.

Sramana Mitra: Where did the seed capital come from?

Jeremy Swift: From anywhere we could find it – friends and family, largely. There were angel investors, but they were more sophisticated angel investors. We were showing some ARR traction to de-risk it. We took checks all along the way, but it was a race against the clock. How do we gain enough traction and build the company fast enough with the resources available to us? We were only a 10-person company. 

Sramana Mitra: In that two and a half years, how much money were you able to pull in?

Jeremy Swift: $2.3 million.

Sramana Mitra: We are now in 2016.

Jeremy Swift: End of 2016, yes. At that point, we were accepted into an accelerator that we thought would give us better visibility for the business. It was through a large global digital agency called RGA. It was in conjunction with West Field. The mix of RGA’s digital presence and practice as well as the retail background of West Field would be interesting.

We jumped into that two years into the business. I spent the 11 of the next 12 weeks in San Francisco. It was a critical inflection point. We got exposure to a whole slew of VC’s to some of the corporate presentations that we did. That put us on the radar of some sophisticated VC’s out there. We were fortunate to get such a ton of inbound activity which led to us raising a really strong Series A which Upfront Ventures led.

A group called High Alpha also joined that round. The interesting thing with High Alpha is this was a venture studio and a venture fund that was founded by the former founders of ExactTarget which is the largest competitor to Blue Hornet and who had the largest single exit out of our category to Salesforce. They saw enough in us that we could be the next ExactTarget maybe. They participated in that round which was a big moment in the business.

This segment is part 5 in the series : Bootstrapping to Exit, Then do a VC-Funded Venture: Cordial CEO Jeremy Swift
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