Yanky (Jacob) Guttman // Nail It Handyman

The kind of entrepreneur that I most admire is one who builds up his business to the point where he does not have to be involved with the company all day. After speaking to Yanky (Jacob) Guttman, I was truly impressed with how he launched and steadily grew his business—and I was a bit jealous of his freedom, too. (It’s right after Pesach, so I’m still thinking about freedom).

Yanky saw a gaping hole in the market and built a business to fill it. While dabbling in interior renovations, he tried to hire handymen for minor jobs and realized that finding readily available, good handymen on any given day was a difficult task. Any decent handyman was too occupied with larger jobs to be able to accept smaller assignments. The more he thought about it, the more he realized that others probably faced a similar problem.

He sat down and wrote up his business plan, envisioning (in detail!) a company that would make it easy for people to find a good handyman. He would hire the handymen and send them out on jobs as they came in. And that’s exactly what he did. Yanky founded his company, Nail It Handyman, and took it from a single truck to a fleet of 30 trucks across several states.

Yanky saw a need, came up with an idea, and created a flourishing business. He totally nailed it…sorry, I couldn’t resist. Enjoy!



“I was born and raised in Monsey, New York. My father is from Williamsburg and my mother is from Monsey, but they both come from families in Eretz Yisrael.

“My father runs the Satmar shul where Rav Chaim Shia Halberstam is the rav; Rav Chaim Shia is the son-in-law of the Satmar Rebbe, the Beirach Moshe. When my father first started there, it was a small shul with about 100 people. Today it is much, much larger.

“I am one of 13, and I was the sandak at the bris of my youngest brother when I was 19. My older brother-in-law was the sandak at the family bris before that. Baruch Hashem, all the zeides and the rebbes had already been sandak for a bris in our family, and the minhag is that one doesn’t give that kibbud twice to the same person.

“In yeshivah ketanah, I had a hard time staying focused. Today, it is very likely that I’d be diagnosed with ADHD, but back then I was just a kid with ants in his pants. I wasn’t a bad kid, but I found it hard to sit still, and I would make jokes in class to create a distraction. It took me some time until I settled down in yeshivah.

“As a kid, I wasn’t that into business, but I did small things here and there, mostly helping out my father. I sold hoshanos, and I helped my father sell matzahs before Satmar Monsey had its own bakery. Nothing crazy.

“The biggest business I ever did as a kid was running a hat-cleaning business before Pesach the year I was 17. I bought a steamer, and I must have cleaned a few hundred hats. It was a lot of money for someone that age.

“I got married at 18 and learned in kollel for the first while. I had no car and no cell phone. My life revolved around going to kollel and coming home. My wife worked near our apartment, and we used to meet at home for lunch. Life was simple, so I saw no need for a cell phone. I know it’s not the norm.

“I enjoyed the world of construction. My father had recently built a house with space for several tenants, and I was a bit involved in that construction, so I thought I could build a small contracting business on the side.

“My father connected me with some people in the industry, and I started telling friends and family that I was going into contracting. I did a friend’s bathroom, and then I did someone’s basement. I put some ads in the local paper and started very small. All I knew was Monsey; I did not think past there. I wasn’t a traveler. I was a real local. I once went to Europe to visit the mekomos hakedoshim, but that’s about it.

“When I started out, I was still in kollel. I’d find a contractor and oversee the work, but I didn’t have to be there the entire time. But as I got busier, I was in kollel less and less. I was in that business for two years, and over time, I realized that there is a real void in the market—the classic handyman.

“The term ‘handyman’ means someone who is skilled at a wide range of repairs. But what happens with handymen is that although they might start off that way, over time they turn into something more like a contractor.

“They start as traditional handymen, fixing things and doing small jobs in people’s homes. But then someone offers them the job of renovating a basement or doing other small construction work. The pay is higher for these jobs, so of course they accept them. And then what happens for the everyday customer looking for a handyman? The handyman tells him that he’ll get to him in a few months when he finishes whatever job he’s in the middle of. I know this firsthand because I tried hiring many handymen for my small business, and I found it increasingly difficult. They were either non-existent, busy or not interested in smaller jobs.

“I saw an opportunity to fill the void and build a business by making traditional handymen who could do classic handymen work available. I knew there had to be other people out there looking for them too.

“The first thing I did was run the numbers. I calculated how much I would pay a handyman per hour, how much I would charge the customer, how many hours we could work per day, and how many days we could work per year. Then I got into more detail: What will the company offer? Which areas will we target? I also figured out how much all the extras would cost, things like equipment, vehicles and an office. I knew I also needed money for basic branding, marketing and hiring employees, and that it would take a year or two for the business to start making money.

“I calculated that in order to have enough capital to get the business off the ground, I would need about half a million dollars. I needed an investor. I was 22 years old, and all I had was an idea and a few papers with some details.

“I approached three people who I knew had some money, and one of them was willing to hear me out. He told me to come to his office, and I presented my idea. He decided to invest in my business, but he said he would make the full amount of funds available to me over a designated period of time. He wanted to see that I was doing something productive with the money before he invested fully.

“I immediately applied for my Home Improvement Contractor License. Every state has its own requirements for handyman licensing. For example, in New Jersey, the laws are statewide, but in New York, they vary by county. I started in Rockland County, New York, so at first I only needed a license for that county. It’s a tedious process, but once you are licensed, you can have many people operate under your license, which is what many small contractors do when they start out.

“When you call a handyman, you probably get to him through the recommendation of a neighbor or friend, but in the world at large, being licensed brings with it a certain level of trust and credibility. Remember, we go into people’s homes. We have to earn their trust.

“My plan was to create the systems and processes for a large business, as if we already had ten trucks on the road, even though I was only starting with a single truck.

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