From employee to 9-figure CEO whisperer

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Meet my ex-CEO, Ayman Al-Abdullah. He joined AppSumo in 2016, and took the company from $5M to $70 million per year in revenue in only 6 years.

Now, as a CEO coach, Ayman helps 7-figure CEOs get to 9-figure by working less.

Here’s his story:

Struggling entrepreneur

Before joining AppSumo, Ayman had started a few businesses–but struggled to get them off the ground. “None of them had taken off,” he said, so he took a traditional 9-5 job.

This was in 2008, and everybody was getting their job offers rescinded. The only jobs that were out there were in Accounting. So Ayman interned at an accounting firm–but immediately knew it wasn’t for him.

“I remember them telling us they were increasing our billable hours from 50 to 60 hours (which meant we had to work longer days). The guy sitting next to me literally broke down and started crying at his desk. I remember going, ‘Holy shit is this going to be my next 40 years?’”

Luckily, Ayman parlayed that experience into a position at Microsoft, where he worked for 3-4 years. He was part of a rotational program and loved that he got to learn new skills.

But eventually, the pull of entrepreneurship was too strong to ignore…

The big decision

“I had saved $50,000 and was planning to move to Thailand to stretch it out a few years,” Ayman said. “But I also recognized that I lacked the skills to launch and scale companies.”

“If you want to be an entrepreneur,” Ayman said. “The best way to learn is to go work for an entrepreneur you respect and admire. It’s better than any MBA or what you can learn on your own.”

Before leaving Microsoft, Ayman recorded two pitch videos. First, to be Sam Altman’s chief of staff (he was CEO of YC at the time), and second, to me (Watch Ayman’s pitch video here).

Unfortunately, by the time we jumped on a call, the position Ayman applied for had been filled. But I told him the whole team was moving over to run SumoMe (our new email capture tool), so we needed someone to run AppSumo.

His eyes lit up and I remember him telling me, “Hey, I think AppSumo has a ton of meat left on the bone.”

Early days at AppSumo

We started Ayman on a 2-week trial. He had to close 2 deals in 2 weeks. We still have people do trials to this day. 

Even though he was still working at Microsoft full–time, he crushed the trial and we hired him.

Ayman was living in Seattle at the time, and moved to Austin with just the stuff in his backpack (this was in 2015, before moving to Austin was the cool thing to do).

“In the first year, our only goal was survival,” Ayman recalled. “Every profit we made at AppSumo went straight to funding SumoMe. It was just me running the show, and hiring help seemed impossible.”

So Ayman got creative.

He paid an intern $15/hour out of his own pocket to take repetitive work off his plate. He then used that free time to focus on sales.

“That decision alone doubled our business,” Ayman said. “There’s always an undiscovered talent out there who can grow with your company. Nothing wrong with hiring college kids who are eager to learn.”

After a year, SumoMe became self-funded and Ayman could finally start reinvesting back into AppSumo’s growth.

Ayman’s proudest accomplishments

Before Ayman, we were stuck around ~$5M in revenue. Under Ayman’s leadership, AppSumo’s revenue skyrocketed from $5M to $70M in six years.

But Ayman’s proudest accomplishment is the team.

“Most tech companies have an 18-month turnover. At AppSumo, we have a leadership team that’s been in place for over 6 years,” Ayman said with a grin. “We’ve been able to build something incredible, but also have a ton of fun along the way.”

And in 2021, we were rated the #1 place to work in Austin for tech.

Now Ayman is a CEO coach helping 7-figure CEOs get to 9-figures.

When I asked Ayman for his advice to founders who want to scale their businesses, he half-jokingly said, “Don’t do it. Sell the business, and get out as quickly as you can. There are better ways to live your life.” Read More