How a Serial Entrepreneur Turned a Problem into a Profitable Business

Hello! What's your background, and what are you working on?

Hello, I'm Nitai. I'm originally from Europe but have been living in the USA for the last several years. I've been building products and companies all my life and am probably someone that people would call a serial entrepreneur. I'm currently running both Helpmonks and Razuna. Razuna is my fifth company and is an open source digital asset management system with over 100,000 downloads a year and thousands of customers.

I've built Helpmonks, my sixth company, together with my wife. Helpmonks is all about helping your team manage their email workload. Many people call a tool like Helpmonks a helpdesk or a shared inbox solution, however I see it more as a collaboration platform. Helpmonks can not only be used for customer support, but also for sales and marketing.


Helpmonks has been entirely bootstrapped and is currently making an average of $50,000/month without any substantial marketing.

What motivated you to get started with Helpmonks?

Helpmonks arose out of the need to organize our workload while running Razuna. Because Razuna’s team is spread across the many different time zones in the USA, Europe, and Asia, we would often reply to the same email two or more times, with no clue when to follow-up or who would do so, while other emails never received a response. Apparently, this didn't give off the best impression and made supporting our customers unnecessarily difficult. In addition, we have a lot of customers with a service level agreement (SLA), and therefore needed a way to let everyone on the team know that certain incoming messages required a reply within a specific time frame.

After six months of scouring the market and trying a variety of tools (Trello, Jira, email groups, and some other mail related apps), I decided to build it myself. As someone who always builds a product around an idea (both a curse and a blessing), it was apparent to me from the start that Helpmonks would not be a tool used solely at Razuna, it would become a product. So from the very beginning, it was built with a product in mind.

What went into building the initial product?

It was easy to narrow down the focus given that I had a clear need for a product like Helpmonks. Initially, I naively thought that the tool just had to capture emails, have the option to assign it to someone, have a business process for SLA customers, and maybe do some other things like look like and behave like an email client, integrate smoothly into the customers' existing infrastructure, and provide some team performance reports.

It turned out that dealing with emails is a lot harder than I thought it would be. Because email is so ingrained in our daily lives and tools like Gmail have evolved to make everything feel seamless and intuitive, it’s hard to imagine how complex and challenging it is to build out all of the background processes that go into creating that smooth and dynamic interface. I could write entire articles on topics like email delivery, email parsing and sorting, or dealing with different mail servers.

I guess that's the beauty of the blissful ignorance that sometimes comes with being an entrepreneur. You look back at this thing you built and realize that you never would have started if you knew how much time and stress and energy it was going to take!

It all boils down to surrounding yourself with the right people.


Speaking of time and energy — Helpmonks was built by my wife and me in our spare time while working full-time on Razuna. For over a year, we spent our evenings and weekends making the backend, frontend, website, and payment gateways, then testing, refactoring and doing whatever else goes into a full-blown product before we were ready to release a much simpler version of what Helpmonks is today.

I feel blessed to have found a partner that shares the same passion as me. Though I'm more the entrepreneur type — i.e. building a product, talking to people, and coding — she is more the detail oriented, system architect and backend coder. This in itself is a great combination, but also has its challenges.

Helpmonks is built entirely with Nodejs and MongoDB, with some optional features also leveraging other open source technologies such as ElasticSearch.

How have you attracted users and grown Helpmonks?

I'm a big believer in being present, and that perception is everything. What I mean by that is that you interact with potential customers anywhere and at any time, even when that means it might interrupt your day or otherwise be inconvenient.

For example, I know that many startup founders do not like to using live-chat. Hence the rise of all those live-chat bots. For us, however, being present on live-chat is one of our core values and has the benefit of bringing us in direct contact with our customers, allowing us to get a feel for what they’re thinking and what they want out of the product. We’ve even hired two more people whose only job is to be present on chat so that our customers almost always have someone they can chat with.

I understand that this approach is not for everyone, but as far as I’m concerned it’s been our number one growth tool. I deploy the live-chat widget on all our sites and within all applications. I get chats from people asking if this is real and if they are really talking to the CEO and founder. When they realize that it is indeed me, they feel like they’re truly a valued customer. Wouldn't you feel great if you were having a problem with a product or app and realized you were talking directly to the person with the most influence in the company? In all honesty, I'm not sure how much longer I can maintain this practice as our user volume continues to grow, but I make sure to read each and every single interaction that each of us has with our customers.


Another part of attracting users is email. As weird as this sounds, email is a perfect marketing tool for me. I'm not talking about email marketing or newsletters, but rather the speed and the response you provide to potential and existing customers.

That said, when we felt that Helpmonks was ready, we started to invite users to an early-access program. We tested Helpmonks with around 500 users for up to nine months. With the two tools outlined above, we were able to gather valuable feedback and then release a more comprehensive version of Helpmonks.

Apart from the obligatory ProductHunt entry, we also used Betalist, Startups List, and a few other outlets to let people know about Helpmonks. Nowadays, people find us mostly through searches or through our blog posts. I know that we have more potential and I'm experimenting with some other "growth-hacks" at the moment.

What's your business model, and how have you grown your revenue?

I think we are in a unique position with Helpmonks, as we not only provide Helpmonks as a SaaS product, but also offer a dedicated cloud server and an on-premise edition. In fact, we are the only company that offers an email collaboration platform as an on-premise solution. Though we live in the SaaS world, many companies have a requirement to host applications on-premise, especially for guaranteed security and privacy.

In line with what I've said about being present and available, we work closely with customers and offer to build some features with them collaboratively. I call this “product sponsorship”, and we provide a substantial discount on building a custom feature that fits the customer’s needs and the system as a product. Customers love it as they get exactly what they want, and we love doing it. It's a win-win situation.

Though many vendors tend to base their pricing on the number of users at a given company, our business model is a little different. Since user numbers tend to fluctuate as employees come and go, we believe that basing pricing on users is an outdated model, and instead base our pricing on something more stable within the organization. In our case, this is mailboxes, so we price Helpmonks on the number of mailboxes, and allow unlimited users.


Additionally, we provide a 50% discount to all non-profit organizations and provide Helpmonks for free to open source projects. We think it’s important to to help and support those who are striving to make the world a better place, and this is our way of doing it.

Just like everybody else, we haven't figured out pricing 100%. In the beginning, we had just one price: $9/month. Once we started to build more integrations with other tools (e.g. create a Trello card from within an email, create a ticket from this email in Github, etc.), we had to rethink our pricing. We ended up switching to a package model and currently provide a "Get Started" plan for $9/month, a "Bliss" plan for $19/month and a "Go Further" plan for $39/month.

We definitely have seen growth since introducing the new plans. While in the beginning, it was all about getting our foot in the door with a $9/month product, we are slowly providing tools that let our users manage their customers better, such as a built-in customer relationship management (CRM) that is currently available in a beta to all customers, and a follow-up email funnel system that we’re planning to release soon. These additional features warrant a different price, and we are experimenting with what we can charge for it.

What are your goals for the future?

As mentioned above, we are adding some exciting features that will enhance working with emails. We figure that you already have a lot of data in your email, so we help you improve that data and provide tools that will automate some of the steps. For example, our CRM, while not a full-blown CRM solution, is tailored for customers that already spend a lot of time in Helpmonks.

Along these lines, and as we need it ourselves, we are working on providing a tool to automate follow-up emails and help with any kind of funnels you may want to create. For example, let’s say you need to send out seven emails throughout the course of a 14-day trial that your customer just signed up for. If you already use Helpmonks to respond to sales and support emails, why not also use it to automate following up during the 14-day trial?

Of course, adding features only goes so far. I'm currently experimenting with different methods to increase traffic, and have contacted some companies that specialize in growth to see what we can do together. I'm still trying to find the perfect ratio (sometimes referred to as the “golden path”) between the growth of our user base and the rate at which I will have to hire more people. As someone who is used to bootstrapping, I find this quite challenging.

What are the biggest challenges you've faced and the obstacles you've overcome? If you had to start over, what would you do differently

I don’t think I’m alone in saying it, but I think that a lot of the issues you end up facing as a business are dependent on the people in your team. Not everyone is an entrepreneur or has the same passion about a particular area that you do. As an entrepreneur, you need to wear many hats in the beginning stages of building your business and often take on a lionshare of the work. If something needs doing, you’re probably the one to do it. Once you start hiring people, even the very first employee or partner, you realize that you have to give them freedom in their area of expertise. This might sound obvious as you wanted them for this particular skill set, but when you are used to doing everything all the time, your delegation muscles can quickly atrophy. It might be that you have a strong opinion on how things should be done, and it can be hard to step back and put the process in someone else’s hands. This is definitely something I’ve struggled with.

Once you start hiring people, even the very first employee or partner, you have to give them freedom in their area of expertise.


On a personal level, I feel that getting older has had an impact on my energy levels. While in my twenties, I could go on coding and meeting with people all day and night. These days, this is just not something I can or even want to do. It takes more time and effort to get motivated and I have different priorities. In short, I’ve become a more selective about how I want to or even can spend my time as I get older, and I think that’s true for most people.

When I was younger, I was much more willing to put up with a customer that was very demanding, even though I knew in my heart that this customer was not suitable for my company. Inexperience (and money) leads you to deal with things you’re probably better off walking away from. As I’ve gotten older, I’ve come to realize that you can’t satisfy everyone, and that any given company and product is not meant for everybody. Nowadays I just tell customers upfront if what they are looking for is not what I can provide. It saves us both time and energy.

These experiences have also made me a much better salesperson as I don’t do "sales" anymore, but rather show them what we have and leave it up to them to decide if they like what they see.

I purposely did not list any tech issues here because I think that those can be changed down the road if need be. However, something that cannot be changed (or at least not very easily) are the decisions you make regarding people. For me, it all boils down to surrounding yourself with the right people. Once you figure out how to find the right people and build a strong, lasting relationships, you can conquer the world.

Have you found anything particularly helpful or advantageous? And what's your advice for indie hackers who are just starting out?

I've read so many books about marketing, leadership, etc., that I can’t remember. That is not to say that they’re wrong or don’t contain valuable information, it's just that they didn’t do much for me personally. The only books that I can recommend are the ones that make you think about yourself. The books of Stephen Covey speak directly to me, especially The Seven Habits of Highly Effective People and First Things First.

Other than that, tenacity is a huge asset. Customers will tell you no, your friends and partners will say no, there will be days when you feel like the whole world is telling you no. But if you are determined and believe in what you do, you can overcome the dark days. I know it's not easy, but it's something that can help when the going gets tough.

You can’t satisfy everyone, and no company or product is meant for everybody.


I also abstain from external influences and distractions, meaning I unsubscribe from just about every email list that exists. I do not listen to the news, and I don’t watch TV or listen to the radio. I figured that if there is something important, I will hear it one way or another.

The same thing applies to our competitors. I don’t research their tactics and certainly do not bad-mouth them. I've heard from several of our customers that they got calls from one of our competitors telling them that we cannot sustain our price model and things like that. I do not understand such practices nor do I engage in them. I think this makes you look weak and unprofessional, and distracts you from making your product the best it can be.

I'm also trying to be very strict with my time. I love going to the gym, so I carve out time everyday to go to the gym. I try to do this early in the morning since it helps me focus on the day ahead and feels great to have started the day by pushing myself. My daily routine usually is to work for one hour and do all the emails and organize my day. Then I hit the gym for an hour, eat something right after, shower, dress, and then start my work day. This is usually around 10-11am. I then work until 7 or 8pm.

I've become a firm believer that you can get everything done in six hours. If you need to work longer than this, then you are doing something wrong with your time and energy.


Many years ago, I stopped working 18 hours a day and started to focus on channeling my energy to 6-8 hours. I've become a firm believer that you can get everything done in six hours. If you need to work longer than this, then you are doing something wrong with your time and energy. Of course, there are days, where I fail and just keep on hammering on a topic, despite knowing that nothing good will come out of it.

I'm currently experimenting with neuro/biohacking. I like the idea of utilizing the body and mind I've been given to its full potential. I also can't sit idle (except when coding), and my mind rattles all the time, so I like anything that goes into engaging my body and mind.

Where can we go to learn more?

You can find out more about Helpmonks over at I'm active on Twitter @thenitai. If you want to talk to me, you can reach me at [email protected] directly.

I hope this interview gives you a glimpse into what I'm doing with my startup. Please feel free to ask me anything in the comment section or contact me directly. I’d love to hear from you, seriously.

Nitai , Founder of Helpmonks

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  1. 3

    From having worked at a (now-defunct) startup attempting to optimize inbox productivity, I can attest email is one tough animal. Congrats on sticking with it to the point of $50k/MRR. Incredible.
    Since this is such a technically complex process, what did your MVP look like? How long did it take before you were able to gather paying customers, and were those all from ProductHunt, BetaList, Startups List initially?

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      Yes, email is a tough cookie :) When I mentioned, that I initially thought it has to do this and that, I've meant it sarcastically. A lot of hours goes into making parsing and delivery correct.

      Regarding your questions, we developed the initial version within a year (we worked also on another project during the day). We let early beta testers use the system after 4 months and tested with them for 9 months.

      After going live, it didn't take long for customers to sign up. I credit this to the blogging I was doing for almost a year up to the initial launch (my first ProductHunt launch only gathered around 40 upvotes).

      Hope this helps.

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    Wow learned a lot .. Thought working 18hrs is a better way to do everything. Maybe for now I will just dedicate 6hrs core for real work then rest of the 12hrs for something else coz I really have alot to get done

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      Thank you. I used to work for 15 years at least 18 hours a day. At one point, it was just not feasible anymore and I had to be honest with myself that most of those 18 hours were not "productive hours", i.e., totally concentrated and immersed.

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    Awesome insight!

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      Thank you. Appreciate the sentiment.

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    Nice work Nitai!

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      Cool. Hope it helps somehow.

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    What kind of successes and failures lead up to these past two busineses?

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      Thank you. Appreciate the comment a lot !

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      Technically true, but there are some things to watch out for here:

      First, it's a little myopic to only look at one day, because life is made up of consecutive days and weeks. What happens if you work a bunch of hours this week but burn out for most of next week and can't work or can't work efficiently?

      Second, not all working hours are the same. Later in the day when you're feeling tired and overworked, you may be less likely to get quality work done. Those extra 6 hours you worked may only be worth 2 hours of normal work. And if you miss out on sleep, your overwork will affect what you do tomorrow, too.

      Finally, work tends to expand to fill the time allotted. If you know you have 12 hours, you're likely to work far less efficiently than if you know you only have 6, meaning even your "good" working hours won't be as good when you're working longer.

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        Couldn't have said it better :)

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      I've been working for 10+ years as a software developer. I've been keeping track of my active productive hours for a long time with tools like Toggl. And I can say that anything more than 6 hours is not healthy. This is breaks, meetings etc. excluded. If had worked 4-5 hours in zone, I consider that day very productive.

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        I also track my programming vs non-programming time using Wakatime and Rescue Time and agree that for an 8 hour work day 4-5 hours of programming time is very productive.

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        Totally agree.

        I just had one of those "moments" this morning. I got up at 5 am and was cranking out two awesome features/enhancements within 4 hours.

        At 9 am I already achieved what I wanted for today and now have no pressure for today and can meet with clients in a "relaxed" environment. Though, it took me two days to carve out those uninterrupted hours :)

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