Ari Rasekh spent the first 15 years of his career as a tech and product leader at large organizations like IBM and digital strategy agency SapientRazorfish (now Publicis Sapient), where he worked on projects for the likes of Mercedes-Benz, FreshDirect, Motorola and Unilever. “All my work has one thing in common, which is I really love building things and running things that ultimately leave a mark,” he says.
But a few years ago, he felt himself craving a change. Not only was he getting tired of working in the more traditional 9-to-5 mode, he had an idea for his own product he wanted to launch: Manor, an app that helps homeowners manage their maintenance. He had worked on a similar app for car maintenance with Mercedes-Benz and, after buying his first home, felt something similar was needed for the new generation of homeowners. He was hoping to add a feeling of modern luxury to homeownership, streamlining the work needed as much as possible.
Instead of quitting his job and going all-in on his company, he decided to take an approach that offered a bit more stability, continuing to cash in on his existing career path while getting Manor going on the side. After about three years of maintaining multiple income streams, Ari raised nearly $1 million in funding for Manor, and finally went full-time on the company earlier this year.
We chatted with Ari about why he chose this path, how he managed two jobs at once, and why he decided to go all in on his company when he did.
Shifting his full-time job into a consulting gig
Ari started this whole journey working with career coach Dr. Michael McCutcheon, who encouraged him to consider smaller steps towards his goal instead of feeling like he had to make a major change all at once.
“He basically helped me realize that I could parlay what I was already doing into what I wanted to be doing,” explained Ari. “One of the things I did with his encouragement was I literally took the same career path that I was on, but just went about doing it on a consulting basis.”
Ari chose this approach—rather than keeping his full-time job and work on Manor on the side—for several reasons.
“As an independent consultant, I could ramp up and down as the needs of the business ebbed and flowed and as my own needs ebbed and flowed.”
One was, perhaps obviously, to have more time flexibility. “As an independent consultant, I could ramp up and down as the needs of the business ebbed and flowed and as my own needs ebbed and flowed.”
But another reason (that many side hustle founders might not think about) was to have more legal flexibility. “I didn’t want a company that I was working for to have all the intellectual property to the business that I was starting—most large organizations will make you sign some sort of limiting contract around that,” he said.
Balancing stability and flexibility
Of course, consulting can be a business in and of itself, and Ari didn’t want to have to spend tons of time doing business development for that side of his work. “Then you’re doing three jobs: the consulting job, starting a company, and searching for your next [consulting gig],” he explained.
Through his network, he learned about a full-time consulting gig for Teladoc Health and jumped at the opportunity, thinking this would provide financial stability while giving him the flexibility he was looking for to launch his company. Even though this meant he didn’t need to secure multiple clients at once, he still had to make sure this job kept going as long as he needed it.
“Initially my contract was for about six months,” said Ari. Two months before the end of that, he started conversations around renewing the contract to make sure he didn’t need to search for another gig—and ended up negotiating a year-long extension to give himself extra stability.
Not giving 110% to everything
“Multiple streams of income sounds very glamorous in certain ways, but when it boils down to it, I was basically working two jobs,” said Ari, who put in a lot of hours in the evenings and early mornings to devote to Manor. “The hardest thing about doing that—aside from sacrificing the amount of time I spent with my kids and wife—was the constant split of my mind space between two different things.” Even if he had the time in the middle of the day to take a call about his startup thanks to his new flexibility, the context switching was daunting.
“Multiple streams of income sounds very glamorous in certain ways, but when it boils down to it, I was basically working two jobs.”
Ari did his best to consolidate parts of his day, devoting larger chunks of focus time to each job. But he also found that part of succeeding at this balance was a mental shift.
“My coach said to me: You’ve got to keep your ultimate goals in mind. If your ultimate goal is to have your business be successful, and you’re getting positive feedback from your consulting job, then at the end of your eight hour day with Teladoc—you know, 4:30 p.m. when you’re feeling tired and you have the choice to do extra work to finish a deliverable for them or start to ease up to save it for Manor—you might need to do the latter,” explained Ari. Giving himself the freedom to do a good enough job for Teladoc but not feel like he has to give them 110% allowed Ari the energy he needed to work on Manor. “You need to be able to give yourself the flexibility to prioritize where you want to put all that effort.”
Communicating what you’re doing (when you’re doing a lot)
Something Ari struggled with early on when making this career shift was figuring out how to talk about his work—when he really had two very different jobs.
“You’re networking, you’re talking to a bunch of different people for your next phase of your career, and you’re trying to figure out with each conversation: How do I present myself to this person? I can do a lot of different things, but what’s the most valuable? What can I contribute the most to this person and what can they contribute most to me, in terms of what I’m looking for?” Ari explained.
Early on, it was sharing his consulting goals that landed him the steady gig he was looking for. With that in place, he was able to shift attention to communicating more about his vision for Manor, which is how he landed the first check that started his fundraising round. After many more conversations where he focused on the startup side of his work, he raised nearly $1 million in funding in early 2023.
Here are some of the biggest lessons Ari has learned while raising his pre-seed round.
1. A good pitch deck is necessary, but its main purpose is to get you an initial meeting (you will rarely be presenting from it). After that, the track record of the founder and of the business are key. I found this template from Guy Kawasaki useful as well as this analysis of Elon Musk’s pitch technique.
2. Leverage your contacts and always be networking. I’ve found this applies whether you’re looking for clients, a full-time job, or investors. A warm intro will have a much higher likelihood of getting a meeting than cold contact. This is why one of the first things my career coach had me do was pull together an organized list of contacts and start reaching out. My first consulting job was a referral via a former colleague. And my first big investment into Manor came from an investor who was willing to back me because he had known me personally for a couple years.
3. Expect to hear “no” a lot. Or, more likely, expect to get a lot of non-committal encouragement since a “no” is actually riskier than “wait and see” for most investors. In those situations you should ask why, or what it would take to get to a yes. That gives you something concrete—a milestone or metric—to follow up about once you’ve made further progress.
4. Embrace the SAFE note. While some investors have yet to embrace them, they have become fairly ubiquitous in the start-up community and are the quickest way to close investment and get to work.
5. Choose investors wisely. They will be involved for a long time and can have significant influence. Just as you’re careful about engaging a co-founder or employee, look for investors who bring strategic resources beyond just dollars.
6. One investor gave me feedback that was both direct and tough, but true (especially in the difficult environment during which I’m raising funds). The best stages to raise money are (a) when you have a killer idea but before you’ve done much of anything because it’s all blue sky at that point or (b) after you’ve hit a home run. In between, while you’re still cranking to find that product-market fit, there’s too much uncertainty and risk. The takeaway: While SAFE’s allow pre-seed stage companies to raise money quickly and on a rolling basis, aiming to raise 1-2 years of runway should give you enough time to show results before you have to get back into fundraising mode.
Taking a risk when the time was right
It was a confluence of factors that led Ari to finally step back from consulting and go full-time on his business.
One was the fundraise, even though it wasn’t actually enough to pay himself a salary that would replace his consulting income. “Your investors want you devoted to the company that they’re investing in,” Ari said. To show his investors he was serious, he started tapering down his consulting to put more time into the business.
“That’s when it made a lot of sense, sort of serendipitously, for me to transition to Manor full-time."
Around that same time, his year-long contract was up and Teladoc was looking to manage risk, so they didn’t want another long-term contract. “That’s when it made a lot of sense, sort of serendipitously, for me to transition to Manor full-time,” Ari says, explaining how his consulting client kept asking him to stay on longer in small chunks, and he had to have a tough conversation to prioritize his business, explaining this was an opportunity he couldn’t pass up.
Plus, the relationship of good work and communication he had built with his consulting client meant they were leaving on good terms. “The CTO of Teladoc said to me, ‘I hope your business succeeds, but if anything were to happen, by all means, give us a call back.’”
Having that safety net made it that much easier for Ari to take the leap and shift from juggling multiple income streams to focusing all his energy on Manor.
Since then, he said, “I’ve worked as hard or harder than I previously have in all my career. I certainly feel like I have more flexibility to control my time as my own boss. However, one of my goals is to get to the point where I can take advantage of some form of leverage (other operators, automation, etc.) such that it doesn’t overtake my life. As Manor grows, I can see having even more freedom by slowly enabling my business to run more independently.”