From employee to 9-figure CEO whisperer

Listen to our full conversation on Spotify or iTunes

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This was in 2008, and everybody was getting their job offers rescinded.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.” 😂

Ayman’s Advice for aspiring CEOs

1- Get clear about what you want

The truth is starting a business (0-1) and scaling a business (1-n) are completely different ball games.

Most founders are better off selling their company–and sticking with what they’re best at (starting and launching companies) or hiring an operator to run them.

The different stages of a company

If you’re determined to keep your company, Ayman advises first defining what success means to you. “Too often, founders build companies they end up hating,” he warns. Know your end goal–whether it’s growth, a lifestyle business, or an IPO.

2- Know who you’re serving

When Ayman started working at AppSumo, we were serving everyone from Solopreneur Sally to Enterprise Ethan. But when he analyzed our top customers, it was actually Marketing Agency Matt. This was someone running a business full-time (not dabbling in entrepreneurship), who wanted to reduce monthly expenses to fixed costs.

“The decision to make lifetime deals for Marketing Agency Matt alone tripled the business nearly overnight,” Ayman said.

Revisit your customer base to see:

Who actually loves you the most?
Who’s not a pain in the ass?
Who spends the most?
Who refers the most?

“The most common pitfall I see CEOs make is building for the wrong avatar,” Ayman said. “CEOs try to sell as much as they can to everyone. But when you sell to everyone, you sell to no one.”

3- Keep the main thing the main thing

Another mistake early founders make is having shiny object syndrome.

I know, I know… we’ve ALL heard this before. But cliches are cliches for a reason–because oftentimes they’re true!

Many founders go into this feast or famine mode (a great month followed by a horrible month) because they keep getting sidetracked by distractions.

Ayman shared an old parable with me about the power of focus:

First-time founders try to serve everyone in the world, have dozens of features, integrate AI, and dominate multiple markets all at the same time. Second-time founders focus on becoming the go-to solution in a specific niche.

4- Focus on cash flow

Apple was founded in 1976. The iPhone didn’t come out until 2008. “People like to look at Apple as an overnight success. But when I was growing up, they were the blue computers that the weird kids bought,” Ayman said. “It took 31 years for them to become mainstream.”

One of Ayman’s favorite lines is: “You can recover from a bad strategy or hire. But you can’t recover from running out of cash.”

Few companies make it past a decade, let alone three. The longer the game, the fewer players there are. Think about cash flow. Focus on survivability.

5- Keep the team lean

When should founders start hiring? According to Ayman, as late as possible.

“You should not be bragging about your headcount,” Ayman said. “Hiring is a sign of failure. Eliminate, automate, then as a last resort delegate.”

At AppSumo we had a rule of 1 hire for every $1M in revenue. If you don’t do that, you’re hiring for the wrong roles.

“When you do hire, hire A players,” Ayman said. “Yes, they cost 50% more. But you need less of them. They require less hand-holding.”

Being cheap with talent is one of the most expensive mistakes you can make.

Another great line from Ayman: “You’re one good hire away from cutting your costs in half and two good hires from a completely different company.”

CEO Resources

When I asked Ayman what he does to learn how to be a great CEO, he replied, “I love looking at past founders and CEOs who have succeeded for decades.”

A few books Ayman recommends:

“Books were my original coaches. I remember buying business books at 13-14 years old for my used car business at the library.”

Ayman’s story is a testament to the power of resilience and constant learning.

He realized he wasn’t where he wanted to be long-term at Microsoft
He identified his weaknesses (and sought out those who were great at those skills)
He didn’t make excuses and got creative when he hired a college intern

It’s been amazing watching him grow into the incredible leader he is today.

Rooting for you,

Noah 🌮