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How to Compete Against Multimillion-Dollar Competitors? Highlight Your Values

When VC-backed competitors swoop in to steal most of your customers, you might be tempted to quit. Not Gavin Hammar. When Sendible’s growth stalled in 2016, Gavin revived his flagging startup by emphasizing the company’s customer-centric values. 

Sendible began as a free email and social media scheduling tool. While Gavin worked full-time as a developer, the business pulled in a paltry $400 a month. But revenue exploded into the six figures when he quit his job in 2010 and focused on his startup full-time. Gavin replaced the free model with a paid subscription exclusively for businesses. 

Six years later, when competitors began gobbling up Sendible’s market share, Gavin faced a hard truth: It wasn’t enough to provide a valuable service anymore. Now, he also had to prove his offering surpassed hundreds of others. To do so, Gavin leaned into his bootstrapping roots and personalized his interactions with customers. 

“Rather than try to be like everyone else, we leaned into being smaller, bootstrapped, and caring about customers,” Gavin says. “What if we could put a face to the brand? What if we could be the smaller, more customer-centric alternative?”

Gavin’s efforts paid off when Sendible dominated the social media management space again. Today, it helps other businesses schedule any type of social media post. Clients track their posts across various platforms and analyze metrics reports to see what’s performing well. 

But Gavin never would’ve achieved this success without his dad asking him to build a basic email scheduling platform in 2008. Read on to discover how the Sendible founder evolved his platform to compete with giants like Hootsuite, HubSpot, and Sprout Social. 

Struggling to Turn a Profit Early On 

When Gavin graduated from the University of Cape Town in 2001, South Africa suffered 30 percent unemployment. It took three months and a family connection before Gavin finally landed a job as a programmer. But the stress and anxiety he felt while unemployed lingered. 

During orientation for that first job, a presenter asked everyone where they wanted to be in ten years. Gavin wrote a letter to himself that promised control of his future: “In ten years, I will have my own business.”

But that wouldn’t occur until 2008 when Gavin’s dad asked him to develop software that would send out automated birthday emails to employees. 

Gavin lived in London at the time, working as a developer. It took him three months to build a software program on the side that used command lines to send automated messages. Named IntelliMail, the platform lets you send virtually any type of content digitally. 

At first, Gavin’s dad would send him a list of employee emails, their birthdays, and the message he wanted to send. Gavin plugged in all the info for his dad and sent the emails. But he soon expanded the program to include text messages and social media posts. The more Gavin worked on it, the more he was certain that other businesses would benefit from the software. 

“The product was ready in 2008, so I bought this old server for ten pounds,” Gavin says. “I bought the server, plugged it into my home router, and turned on the website. I renamed it Sendible because it meant sending anything is possible.”

This first version of Sendible was a free scheduling tool used primarily for emails. During 2008, Gavin added the SMS and social media post features as these platforms grew more popular. 

A screenshot of the earliest version of Sendible, circa 2008, when it was a free messaging and scheduling platform

Anyone could sign up for an account and schedule posts at any time. Gavin planned to monetize it by having businesses pay for ads. 

While thousands of free users signed up, few businesses did. Gavin gained publicity through published articles on Mashable and TechCrunch, but these articles didn’t attract paying businesses or agencies, only free users. 

“The VC said, ‘No, you’ll never make a business out of this thing,’ and I wanted to prove them wrong.”

He needed to increase his marketing volume to reach more potential clients. Between juggling a developer job and Sendible’s software, though, Gavin couldn’t dedicate time to extensive campaigns. So he tried appealing to one VC for funds to invest in marketing. 

“The VC said, ‘No, you’ll never make a business out of this thing,’ and I wanted to prove them wrong,” Gavin says. “I kept building and bootstrapping it in my spare time because I still had a full-time job.”

Stay Employed or Risk Everything?

Since the VCs refused to back Gavin and Sendible struggled to attract paying customers, Gavin kept his full-time job as a developer. The company he worked for in 2009, however, demanded that he hand over half of his business to be able to keep working on it. His contract specified that if he registered a business, he had to gain permission from his employers, and if he refused, he’d have to find a new job.

“I was bullied into giving them equity,” Gavin says. 

He negotiated them down to 10 percent in equity and more time to work on Sendible during business hours. But he continued building the startup in his free time too. 

“I was miserable and losing motivation. I kind of gave up on Sendible at one point,” Gavin admits. “The company was still getting dividends from my profits. Why was I working crazy hours until four in the morning? These guys took advantage of me.  

“And so I decided that either I would quit my job and get the shares back or give up the company. Why should I work for them to get something for nothing?” he adds. 

Ultimately, Gavin’s girlfriend (now wife) decided for him. She reminded him how much he wanted to run his own business and be his own boss. Sendible was his baby, and she didn’t want him to give up on it so quickly. They could live off her teacher’s salary if they had to, and they had enough savings for six months. 

“I spent over ten thousand pounds to buy back the shares,” Gavin says. “Just to motivate me to keep going.”

Little did Gavin’s girlfriend know that nearly all of those savings would go into buying back those 10 percent shares. Gavin quit his job in 2010. His old employer had stood in his way long enough, and it was time for Gavin to dedicate himself to Sendible full-time.

“I spent over ten thousand pounds to buy back the shares,” Gavin says. “Just to motivate me to keep going.”

New Year, New Sendible

After quitting his job, Gavin completely revamped Sendible’s service. Instead of a free social media scheduling platform, he converted it into a social media management platform exclusively for businesses.

Rather than sell directly to companies who might use Sendible, he offered to whitelabel it to B2B businesses offering similar tools. They would rebrand Gavin’s software and then sell it to their clients as if it were their own. This tactic alone bumped Sendible’s revenue up from a measly $400 a month to over $100,000 annually by the end of 2010. 

A few factors helped Gavin’s whitelabel services take off. He attributes the end of the 2008 recession as one reason why clients were willing to invest in social media management tools. While businesses were reluctant to partner with him at the height of the recession, they now wanted to grow through any means possible, including social media. 

He also pointed out that Sendible’s dashboard was less recognizable than companies like Hootsuite’s, so he could get away with whitelabeling to more clients.

“Whitelabelling played a massive part in getting Sendible off the ground,” Gavin says. “As a solo founder, I would’ve needed a big sales team to try other marketing strategies. But I couldn’t afford to hire people. Whitelabelling meant that the agencies could resell it for me.”

By 2011, sales increased enough that Gavin hired his first paid intern. This intern helped him with the whitelabeling, fixed bugs, worked the customer service live chat, and so on. Eventually, Gavin added a marketing manager, more developers, and a head of sales. All of these employees helped Gavin redesign Sendible in 2013, improving the front end and user experience so it could keep up with modern standards. 

“We streamlined the whole platform to give it more of a dashboardy feel,” Gavin explains. “We created a big composition box to let you compose across multiple social platforms.” 

These improvements fueled Sendible’s growth until 2016 when well-funded businesses entered the social media management space. 

Don’t Model Yourself After Your Competitors 

At first, Gavin tried to keep pace with his competition. He hired six new salespeople just to cover outbound strategies. But customers continued flocking to Hootsuite and Sprout Social. These VC-backed companies and others like them could afford aggressive marketing campaigns. 

Gavin’s bootstrapped business couldn’t keep up, but that was okay with him. Rather than copy all those big businesses and their marketing strategies, Gavin focused on Sendible’s unique selling point (USP). 

Unlike other social media management platforms, Sendible emphasizes human connections in its client interactions. Paying customers feel understood because all customer interactions are handled by real people, not an AI. Leaning into that personal touch could allow Sendible to stand out, Gavin thought. 

He tested this theory by replacing stock images on his website with photos of his employees working in the office. Real people also took over customer service from chat robots or AI systems, and the support team recorded Loom videos to build trust. Gavin carried over more videos into the general website so that customers could see his employees at work. Instead of meeting clients at giant trade shows, Gavin rented bars for intimate client gatherings. 

Sendible’s monthly recurring revenue tripled. He hit seven figures in 2020, and the business continued to grow until Gavin received an acquisition offer that he couldn’t refuse. 

Selling One Business to Kickstart Another 

After spending more than a decade building Sendible into a top social media management platform, Gavin decided to sell the startup in 2021. 

“As a bootstrapper, I never planned to sell. I’d always wanted to just build this company for fifty years and keep it going,” Gavin says. “But after Covid, I thought it was time to sell because most SaaS companies’ growth had peaked at that time. I accepted one of the offers and sold the company. And I can attribute that offer to all of the brand-building we did.”

Leaning into his bootstrapping roots and customer-centric values helped Gavin build a profitable business. Other founders noticed his success and offered to invest more resources into Sendible to grow it further. 

Gavin missed the early startup stages of building a business. He wanted to create again, not just work on admin operations. With new founders offering to scale Sendible the way it deserved, he knew it was time to pass the company on to someone who could execute a bigger vision for it. He started the due diligence process and spoke with a broker to get a valuation on the company. 

“Our high EBITDA margins and our downward churn trend allowed us to get a very good valuation. Also, the deal was all cash and allowed me to walk away from the business after a six-month handover,” Gavin says. “I didn’t use any platforms like MiroAcquire, but I would’ve loved to.” 

Instead, Gavin handled the acquisition alone, running through the code to collect data points and metrics. He did so secretly, without informing his employees, because he wanted the acquisition to go through first. 

“Doing things behind their backs was a bit hard because I was always so honest, authentic, and open with the team. So having to creep around and get the numbers and do this deal behind their backs made me feel uncomfortable,” Gavin says.

“I had to announce it on Zoom in front of 50 people. And their faces were just white. People were crying because we were such a close-knit team and a family-type of culture,” Gavin continues. “They found it difficult to adjust to the fact that Sendible’s owned by a private equity firm after starting as a founder-led company.” 

But Gavin wouldn’t have gone through with the acquisition if he lacked faith in the buyer’s ability to take care of the business. He says that the employees are now “happy and thriving” under the new management. 

After his six-month handover ended, Gavin focused on a new business he’d been toying with called StoryPrompt. While he might look at StoryPrompt as more of an asset than a passion project, Gavin can’t deny that he’s excited to start fresh. 

“I can’t wait to build again and get my hands dirty,” Gavin says. “With Sendible, I had a team of people who own all different parts of the company. So I couldn’t touch the website, play with code, or test things because we’d gotten so big. It allowed me to step back very easily, but I lost that creative spark because of all that growth.

“So for me, just building again, getting my hands dirty, experimenting, having complete control again, is lots of fun.”

With 12 years of experience under his belt, Gavin now advises other bootstrapped founders on how to build a thriving startup. His podcast, Unscalable.fm, allows him to connect with other founders about creating customer-centric businesses that grow to exit. Gavin offers first-hand insight about the triumphs and challenges he faced with Sendible, coaching these founders so they can confidently compete with VC-backed competitors and still stay true to their values. 


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Leanne Stahulak
Leanne Stahulak
Leanne’s love of books inspired her to become an author at a young age. Though she began as a creative writer, Leanne also built up her skills and experience in journalism at Miami University. After graduating with three degrees, she now tells founder stories at Bootstrappers and writes about growth and entrepreneurship for MicroAcquire.

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