From 0 to 19,000 users in 2 years with BookLikeAboss CEO & Co-founder, Nachum Kligman | Yuli Azarch

From 0 to 19,000 users in 2 years with BookLikeAboss CEO & Co-founder, Nachum Kligman

Yuli Azarch Yuli Azarch | July 1, 2019 | No Comments on From 0 to 19,000 users in 2 years with BookLikeAboss CEO & Co-founder, Nachum Kligman

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“Being an entrepreneur is about taking risks. — Nachum Kligman”

Nachum Kligman is the CEO and co-founder of Book Like a Boss. It is a service which helps people to book meetings. Nachum is also the publisher of which is a media website for entrepreneurs. He is also an author, speaker, and entrepreneur.


What We Discussed On The Show?


Nachum’s Background.

Nachum is a born entrepreneur. He was always the kid that was shoveling snow for twenty bucks and selling baseball cards at trade shows. He was always looking at how to make money. Although he was a terrible student, he was very street smart. Nachum’s first real business was in the advertising specialty space.

In 1999, Nachum had an idea for an auction type of software. But it didn’t work out because it was illegal. In 2002, he started an interoperable instant messaging company. It had its own instant messager and had RSS feeds. Although the massaging platform was a good business, Nachum had a vision towards social networking. He wanted to shift, but his co-founders turn his vision down, so he decided to leave the company.

In 2005, he started another company called Viewbix. A company about monetizing video, not through advertising but the video itself as a selling tool. He had three patents for this company.  He sold 80% of the company ownership for $250,000.

The company exited at the end of 2018.

“I believed in technology and I put so much into it. I wanted to see it exist. I didn’t want my employees to leave. But he [the dealer] made such a bad mistake because I was the visionary in the company, and I went from owning 75% down to 4%. So my heart wasn’t there anymore, 6 months later, I left the company.”

According to Nachum everything you’ll learn as an entrepreneur is that there is no such thing as a failed company unless you fail to learn from it.


The No Fear Mentality. 

When Nachum was younger he was constantly bullied by a neighborhood kid. He used to beat him up and made fun of him for years. One time he came crying and his grandmother was there and what she said to Nachum changed his life and made him an entrepreneur.

“She said, hit him back.”

The next time he started bullying, he just pounced on him and started punching him. He was pouring out all his frustrations and all that the bully could say was: “what took you so long?”

This event changed something in Nachum’s head. In the beginning, it was more in a negative way, because he started getting this attitude like “I don’t have to let somebody hit me, as a matter of fact, I can do whatever I want. It’s my life and I don’t have to listen to anybody.” Although this attitude got Nachum into a lot of trouble, it also allowed a “no fear” mentality. He didn’t care about what anybody said.

According to Nachum, as an entrepreneur, a lot of people will try to rain on your parade. They’ll tell you that it is impossible. But because of this attitude, Nachum decided to take risks. He would do things that you most normal people wouldn’t do.

Still today, he doesn’t care about what people say about him. From a business sense, Nachum is not worried when somebody says something negative or complains about him. According to Nachum, the more successful you are, the more people will talk down to you.


The Birth of Book Like a Boss.

Being that entrepreneur inside him, Nachum always liked new challenges and doing new things. After going from startup to startup, he decided to take a break, start a podcast, write a book, and do some coaching on the side.

Of course, the book and the podcast did well. So Nachum started to get lots of phone calls and emails of people trying to pick his brain. At that time, he was charging $250 an hour for a meeting.

He thought of an idea, a way to just send somebody a link. When someone wanted to meet with Nachum, he would send them a link to book him. Not just a calendar, but a page that said, “this is who I am, this is what I do, this what other people say about me, here are the most frequently asked questions.” It was supposed to be like a landing page for bookings.

He started to see the unmet needs related to that.

“That’s when the light bulb went off, I said, if I as a business coach, have this need and her as a masseuse has this need… I said I bet there are hundreds of thousands, if not millions of other people that have this same need for an easier platform to sell services”.

A top-of-the-line programmer became available. Nachum told him about the idea, and he immediately said yes, let’s do this. Three months later, they already had some code and realized they needed a designer. They spent the next year and a half building the first prototype of Book Like A Boss.


Gaining Traction.

Originally, Nachum Kligman and his co-founders did not want to be an appointment scheduling service, they were not looking to be the next Calendly. The original idea was focused on selling a service so that, for example, if you’re a tutor you can create a page, a calendar, and let people book your tutoring session and pay you from a session.

But according to Nachum, it was hard to explain to people what is it that the product did. At that time there wasn’t something similar, so they decided to add appointment setting features so that people would say “I get it it is like Calendly, but they offer more”.

Once people understood who they were, they were able to upsell them on the other services that they offered.

“I tell everybody, especially when speaking about entrepreneurship, that you got to find the pain-point… and then you got to say, would people be willing to pay for that pain point.”

You may solve a pain point but if it’s a hundred thousand people, nobody is going to pay for it. Can you solve a pain point, and can you sell it in a way that people will be willing to pay for it?

For more information on the story of Book like a Boss, visit the About Us page.


Validating the Idea. 

Nachum knew instinctively that this was something that was going to be big. He saw where the market was going and where the economy was going. He said that 50% of millennials have their day job and a side hustle, so he knew this was a good deal.

They launched at AppSumo in 2017 and went from two to three hundred users and later to five thousand users in three weeks. The had very slow growth but in three weeks, they were able to validate their product. According to Nachum, they got tremendous feedback from those initial 5,000 people. They continue building and improving the product after that customer feedback.

“We were growing viral without spending any money, because of the power of our branding.”

It took about 14 months to gain customer traction. Nachum knew that this is was something that had lots of potential and that could solve lots of pain points.

According to Nachum, it was frustrating because for a year-and-a-half they didn’t get any income. Nachum and his partners were doing side work and were building Book Like a Boss as a side hustle.

It took about a year before they got their MVP.

“The first time that I got a paid booking and it was $250 for an hour coaching session and I was just like, wow, this really worked this is exactly what I wanted, that first time that I sent the link and someone, he looked at it, book me, and paid for it… I was like, I built this for me.”


Solving a Pain Point.

According to Nachum, the pain point is key. If it is your own pain point, you’re going to be more passionate about it because you intrinsically know the pain. According to Nachum, you can hear about some else’s pain point, look at the market and say hey, “this is missing if we did this and it could become successful.”

But if you yourself are experiencing the pain point, then it becomes part of you and solving it is like selling it to yourself, you’re very close to it and you know exactly what to do and how to do it because you know what you need to know in order to solve that pain point.

“When we built this company we said, we are going to be bosses, we are going to run things, we are going to bootstrap. We are not going to take VC money. We are not even taking investor money until we have proven that we can make money with it.”

Early on investor was willing to give $100,000 for 10% of the company and Book Like A Boss founders were willing to take the deal, but he wanted really a board seat. Nachum told him no because he knew from previous experiences that once you have a board seat you have influence and you can start making decisions. Nachum and his co-founders didn’t want anybody else making decisions.

Being Bosses became part of their theme, part of who they were, their attitude and part of their breadth. Nachum calls his users, bosses. They have over 3,700 passionate bosses in their Facebook group.


Running Away from VC Money.


According to Nachum, for VCs to invest in you, you need a technological advantage. You need to do something different from anyone else from a technological standpoint.

Book Like A Boss is very focused on listening to their customers and about creating great products for them. The VC firm didn’t invest in them because they don’t believe in that. According to Nachum, VCs are after the home run, the 600 million, or the billion. 

Nachum and his co-founders preferred to take money from angel investors and run away from VC money. Another case of why running away from VC money might be your best choice, is the story of Rand Fishkin.

“Our first investor that put in $200,000, he is thrilled, he saw what we were able to accomplish with that funding for two years ago.”

But without capital, there is only so far you can go. According to Nachum, they want to raise some more capital, bring in more developers, and start doing PPC campaigns.


Running Slim.

Nachum, recommends not to be skimpy on the things that matter most to your company.

So if you need a developer, trying to offshore your development is not going to be good for the long run and you are going to have more problems.

If you have a tech company you, have to have someone that has tremendous skin in the game and loves the product to really build that out and put in the thousands of hours needed.

As for today, Book Like A Boss is composed of three team members. Nachum went with a top-of-the-line programmer and designer as co-founders. He wanted to have top professionals and team members that have a passion for the product.

Instead of hiring an employee, they hire contractors or company. They hired one of the best SEO and affiliate management companies.

“When you work with the best, it’s fewer headaches and you know you don’t have to babysit and you could just let them do what needs to get done”



Why Build a Good Foundation?

According to Nachum, you have to have a solid foundation to build everything else on top of. The coding has to have a solid foundation, and it has to be good quality. The design has to be good quality.

Anything that will set yourself up for success, has to be done right. Nachum believes that if you can get onboarding and the funnels right, then you can start working on automating things more properly.

“Because you can’t really scale until you have those foundational things in place. There is no point in driving traffic if you can’t control the users as good.”

Nachum recommends to first do what you need to do to up conversions, then you can worry about scaling and bringing more users. You have to do things that are actually going to bring you in money.

Because if the company does not have money, it can’t keep going. Which is probably one of the top challenges of a bootstrap company. Nachum believes that if you want to be successful, grow,  and take care of your customers, you got to make money.


Show Notes:

  • Appsumo to promote products and services.
  • Book like a boss, to schedule services and book appointments online.
  • Book Nachum through
  • Nachum recommends reading anything by Gary V, Tim Ferris, Richard Branson.


Thanks, Nachum

Find him at Book Like A Boss. He recommends signing up for a 2 weeks free trial. Or you can also find him in or book him through


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