"I pitched to one VC, that was enough. I wanted to prove that I could do it on my own."

Gavin Hammar, Founder of StoryPrompt

Gavin Hammar
Gavin Hammar, Founder
London, England, UK
Go-to-market, Founder journey, Bootstrapping

About Gavin Hammar

In 2008, Gavin bought a second-hand server for £10, plugged it into his home router, and launched a website called Sendible. Since then, Sendible has gone on to become a leading social media management platform, reaching 8 figures in recurring revenue, more than 30,000 users and 50+ employees.

Unlike a lot of tech entrepreneurs, Gavin did not raise any outside capital and has proven that it is possible to beat the odds and build a successful, profitable company in an extremely competitive market while remaining fully bootstrapped.

A lot of what made Sendible stand out in this highly contested space is the fact that Gavin was able to help the company portray a more human face amongst so many well-funded, faceless competitors.

Sendible's incredible growth and recognizable brand attracted the attention of Traject, a suite of best-in-class marketing technology companies, and the company was acquired in 2021.

After leaving Sendible at the start of 2022, Gavin launched his new startup, StoryPrompt. StoryPrompt is a video engagement platform that makes capturing customer stories, testimonials, and attention as simple as sharing a link.

Post Acquisition Learnings After 12 Years Bootstrapping | Gavin Hammar, StoryPrompt

Resources mentioned on this episode

About this episode

In today’s episode, Melissa sits down for a (virtual) drink with Gavin Hammar of StoryPrompt. After Melissa pours her lemonade and Gavin his Brewdog, Gavin shares his backstory with Sendible and why he chose to sell the company. He is from Cape Town and moved to London in 2005. He founded the company Sendible, which grew to 30,000 users and was rated as one of the top tools in their category. However, Gavin never planned to start a business of this scale and happened on it mostly by chance. The tool was free for customers to use for scheduling blog posts and businesses would receive compensation for their ads on the posts. He quickly attracted 20,000 users after a few write ups about the new tool. Eventually, Gavin quit his day job to focus on Sendible full time.

Next, Gavin identifies some of the major shifts he experienced during his decade at Sendible. Between the years of 2008-2010, he was only working on building the actual product to be released. This entailed many long nights alone at home for Gavin as he tried to work through all of the kinks. When he first launched in 2008, businesses were not really on social media. It took some time to find the proper product market fit for the service. His first employee hired was a marketing manager. In the first few ears, the company experiences a large amount of growth and success. However, by 2016, there were so many huge competitors in the market and their growth had stopped. Amongst these faceless, sleek competitors, Gavin decided to do something different and put his employees’ faces to the company name. Rather than bots greeting users on the website, it was now the team members themselves. In each of their touch points with customers, they put their own personal spin on things.

By 2018, the company had started to see the results of this new marketing strategy. Gavin was being contacted by many organizations who were interested in purchasing Sendible. The more he considered it, the more he felt like taking a step back from Sendlible was the right thing for him to do. He came up with a list of criteria he wanted from a potential buyer and when checked those boxes, he agreed to sell it. Then, he reveals what it was like to watch someone else run the business he had created and worked on for so long. He observed them making the same mistakes he had made in the operations several years prior. Watching the company change without having any say in it was very difficult for him, which is why he started a brand new company soon after.

Shifting gears, Gavin shares his most important lessons learned from the process. First is the importance of hiring to fit company culture and values.  Second was the mistake of hiring friends to work alongside his other employees. Finally, he learned no to hire people he couldn’t afford to train. Don’t miss his advice for bootstrapped founders who are building their own teams today. What made Sendible such an attractive company to work for was their employee benefits and perks.

Before wrapping up, Gavin gives a look into his newest company StoryPrompt, which helps brands build strong relationships with their customers, employees and their community through asynchronous face to face video communication. He built the company during Covid as a way to bring faces back to companies during the days of lockdown and fully remote work. The biggest thing he learned while at Sendible was the importance of community. He also learned that you must be creative in your marketing strategy to garner traction and attention. You must plant seeds now in order to bear the fruits later on. In closing, he leaves listeners with final words of wisdom on driving growth and profitability. 


0:55 - Welcome to this episode, in which host Melissa interviews Gavin Hammar.
3:09 - Gavin’s story founding Sendible.
9:40 - Why Gavin chose to bootstrap Sendible.
12:03 - The major business shifts Gavin experiences in his decade with Sendlible.
16:15 - Why Gavin started to consider selling his business.
21:38 - How Gavin felt after selling Sendible.
24:40 - Watching someone else running his project.
26:55 - Gavins shares his lessons learned.
29:49 - Advice for bootstrapped founders building a team today.
33:25 - Gavin’s new company, StoryPrompt.
37:50 - How Gavin is applying previous lessons from Sendible to his role now.
42:11 - Gavin offers final words of wisdom.

About ProfitLed

Welcome to the ProfitLed podcast, where we discover proven growth strategies for bootstrapped entrepreneurs from the people who have done it before to help you accelerate your business! The ProfitLed podcast is brought to you by eWebinar, the leading automated webinar tool, and hosted by eWebinar Cofounder and CEO, Melissa Kwan.

ProfitLed is forum for the unsung heroes of SaaS, the founders and others behind the bootstrapped startups who are creative and resourceful enough to forge a pathway to success. Here’s where they get to share everything they learned along the way, so you can benefit from their expertise and find success in your ventures, too!

Learn more about your host, Melissa Kwan, and the ProfitLed podcast.
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eWebinar, webinar, SAAS, founders, Sendlible, StoryPrompt, entrepreneur, founder story, bootstrapped, startup, blog, bootstrapped companies, funding, storytelling, product market fit, social media, technology, product marketing, company growth, social media tools, customer relationships, software development, coding, innovation, company culture, hiring, brand messaging