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Best of Bootstrapping: VC-Funded Venture After Bootstrapping to Exit

Posted on Wednesday, Jun 25th

A very effective way to dance the entrepreneurial Waltz is to do a bootstrapped company first, sell it, and then do another venture with a more ambitious agenda. From 2021, Jeremy Swift’s journey as Co-founder and CEO of Cordial is a great case study of this method. Sramana Mitra: Let’s go to the very beginning of

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Best of Bootstrapping: Bootstrapped to Exit and THEN Did a VC-Funded Venture

Posted on Monday, Sep 18th

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page.  A very effective way to dance the entrepreneurial Waltz is to do a bootstrapped company first, sell it, and then do another venture with a more ambitious agenda. From 2021, Jeremy Swift’s journey as Co-founder and CEO of Cordial is a great case study in this method.

Read Full Article »

Best of Bootstrapping: Bootstrap to Exit and THEN do a VC-Funded Venture

Posted on Wednesday, Mar 23rd

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page.  A very effective way to dance the entrepreneurial Waltz is to do a bootstrapped company first, sell it, and then do another venture with a more ambitious agenda. Jeremy Swift’s journey as Co-founder and CEO of Cordial is a great case study in this method. Sramana Mitra:

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Bootstrapping to Exit, Then do a VC-Funded Venture: Cordial CEO Jeremy Swift (Part 6)

Posted on Monday, Nov 22nd

Sramana Mitra: Once you had the Series A, what was the next major inflection point? What strategic moves did you make to get to that? Jeremy Swift: I would say it was about just further refinement of what our ICP was and figuring out go-to-market too. That was a hard thing to navigate. It took

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

Posted on Sunday, Nov 21st

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

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Bootstrapping to Exit, Then do a VC-Funded Venture: Cordial CEO Jeremy Swift (Part 4)

Posted on Saturday, Nov 20th

Sramana Mitra: I was recently talking to the founder of HubSpot. His observation when they started was that people were trying to do inbound marketing by starting blogs and then tying together some level of CRM. He said that nobody had an integrated solution, so he chose to build one. None of the categories that

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Bootstrapping to Exit, Then do a VC-Funded Venture: Cordial CEO Jeremy Swift (Part 3)

Posted on Friday, Nov 19th

Sramana Mitra: You were getting ready to start something else, but you wanted to develop some sales chops. Where did you do that? Jeremy Swift: I actually told this mentor that he’s crazy. I spent the next year or two warring against that. I finally came back around and this mentor said, “You got to

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Bootstrapping to Exit, Then do a VC-Funded Venture: Cordial CEO Jeremy Swift (Part 2)

Posted on Thursday, Nov 18th

Jeremy Swift: I worked full-time during the day. I started waning on college. I was talking to advisors and told them about it. An advisor in the Comm department and another from the business department both sat down with me and said, “We understand your personality and what you’re interested in pursuing. We’re going to

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