Ask HN: I am doing $2M annually as a solopreneur and need your help

I would love to be in your position.

My deepest, most honest urging to you is to NOT do what you are contemplating.

Just keep doing what you are doing for as long as you can and take the cash out and put it into stable investments for your retirement. By a nice house and car, have holidays, take care of your family. Use this to complete the task of gaining financial independence for the rest of your life. When that is well and truly done then sure, treat your business as something potentially disposable and turn it into a "company" - but even then I would not advise that.

I have done the company thing and always regretted not keeping it one-man-small and just milking all the cash out.

You are sitting on an incredibly valuable thing to you personally. Don't blow it by spending all the good cash on making a company.

The whole point of being in business is to make money for YOU. You have succeeded, you are past the finish line of my ultimate goal. Do not employ even a single person.

The fact that you are inexperienced in running a company emphasizes my point tenfold.

I agree with the others who have pointed out that you're already successful, don't break it!

That said, don't even consider HR as your first hire. Not even for a second. Their role is to police contracts and resolve issues. You won't have that until you have more people.

Get someone who wants to do the stuff you are tired of doing.

Take it from Sam Altman: don't hire employees [1].

[1]: https://youtu.be/CVfnkM44Urs?t=473

Is there a way for you to restrict access(limited access) to these accounts?

I'm interested in hearing what others have to say as I have been wondering this myself about giving away sensitive account access. However, I would have to side with hoodoof. You're in a position right now that's a sure thing and it's bringing you money. You never know what lies beyond so I would milk it as well. Yes, you can find even another source of income just as lucrative, if not more so, but you can also wind up not finding anything and losing your current income. Be careful not to underestimate how difficult it is to get to where you are with your current business just because you're able to do it once. It's well known that luck plays a huge roll, and with that said, I wish you the best of luck.

This lecture series specifically talks about the different problems faced at various stages of scaling, and it includes a lot of reputable people who have actually done it:

https://www.youtube.com/watch?v=s3RrVmv5WwA

The YC series is of course good too:

https://www.youtube.com/watch?v=CBYhVcO4WgI

I'm not actually qualified to answer your question, but it sounds like you haven't discovered a bottleneck in your business yet, and until you do, you probably shouldn't hire any employees.

If you are going to leave being solo, don't start by bringing in people from the top. Start with the bottom.

Define one or two jobs that you are doing now that can be spun off. Perhaps customer support or material writting. Document how to do that job, then bring someone in, train them, learn how to manage them, and update you docs with what you learn that you've missed.

In this way you stay in control, you can back out if you need to, and you can gradually replace yourself with systems.

A good book on doing this is the oddly named "E-myth revisited". Just don't take everything in the book too literally.

--

Remember, a startup is a search for a product that people want to buy. You already have both. That means that much of the startup advice is actually posion your company. Listen to your gut.

And good luck! I wrote a backend system for a training and certification company - I'm familiar with the nutso profit margins.

I do a lot of work helping early and mid-stage companies scale their workforce and technology. Some companies scale by the seat of their pants: they hire people for specific needs as they arise (e.g. servers crashing, or too many sales requests coming in). Other companies scale in a more organized, planned process, like having a big vision of becoming a global company in 5 years. In both of these scenarios, especially because you don't have a co-founder, you're going to find that it's hard to give your #2 hire a sense of agency. You'll likely feel disappointed in their style (different coding practices, different customer interactions, etc.) and want to micromanage. To help with this, start them off on a non-mission-critical project (like expanding to a new region or building a feature that's been in the backlog), and be clear with them about what "success" means for that project. Having the definition of success be written by them, in their words, will also help ensure a two-way communication here. After they have a successful project under their belt, you'll find it easier to trust them with more important work. Also keep in mind that right now you have a product, but when you hire your second employee, you'll also be establishing a culture, so it's worth putting thought into what culture you want to promote.

I'm going to disagree with some of the sentiments here. There are a number of tasks that you are more or less wasting your time on every day because you could hire people to do them, thus allowing you to free up your time to focus on what your competitive advantage is. It's really important that you called these things "chores." That says a lot about those tasks.

What you don't want is to hire a bunch of people you don't trust with any responsibility - that's a recipe for micromanagement, which is even more of a waste of time than doing the "chores" to begin with!

Take a long time to hire someone, but hire someone who can take the largest percentage possible of tasks off your plate. If you're worried about data loss, have backups. If you're worried about credentials, make separate accounts with different access. But you need someone who you can trust, who you feel like is smarter than you at some useful set of skills. Someone who is as passionate as you are about what you do, and hungry to make a good impression.

I was an early employee at a startup that was acquired less than two years after I joined. We grew from seven to seventy employees in about twenty months. My contact info is in my HN profile if you want to know more.

You don't provide enough detail for specific suggestions, but it sounds like you would benefit from having a mentor who has been down this path before.

Another way is start inviting smart and experienced people to lunch to bat around ideas. You don't even have to know them personally - a lot of people are glad to chat casually over lunch in the spirit of helping fellow entrepreneurs.

After having a few discussions like this you'll be able to see things from multiple perspectives and choose the best path to fit your business.

This will cost you nothing but lunch in exchange for some very valuable advice.

Outsource as much as you can (except the financials/accounting, unless you can find a trustworthy accountant).

Your first hire should either be someone that complements you, or that does your job (redundancy/"fault tolerance").

If you've managed to survive without a co-founder, then keep going without one. If someone ends up with enough responsibility to be the equivalent, then make them COO, CTO, CEO, or something along those lines.

Can you share any additional details on your business? Do you sell an elearning book or is it a full on subscription? Would love to know any additional specifics you'd share.

I going to be in the Don't category on this one.

However, if you are really set on doing this, you should list all the stuff you don't want to, say like pay bills, working deals on the phone or support. List the things you don't like doing and then see if you could bring in one person to handle those jobs. Not a manager, but someone you could quickly train and easily manage. Start farming things out to them and when they hit capacity, possibly hire another person who can handle the other stuff you don't want to do.

You have an incredible opportunity here. You are profitable, now you just need to start adding people on to handle the stuff you don't want to do and then you are free to do the things you want too or need too. Don't grow your staff for the sake of growing your staff to convince yourself you run a "real business". You already run a Real Business.

First goal should be to get rid of the tedious small tasks, allowing you to focus on core responsibilities. Pay for a virtual personal assistant on the other side of the world to do menial tasks for you while you sleep.

After that, I recommend meeting with other medium-size startup CEOs in your region and getting their advice for what role could provide the highest leverage for your company.

I was in a very similar position to you about 2 years ago. I was running a company on my own doing great with revenue and profit. Currently, I have a 6 person company.

The way I ended up expanding was first starting to work with one other really great person. I ended up needing a professional sales side to the company and Lizzie came in and did that. She was also better and more experienced than me at hiring and managing others, so luckily, she was able to hire the person that is now my lead programer as a second critical hire.

Then we hired on two more developers.

During this time, the people I had that were "helping me with my chores" originally did more and more of that and began helping with other random areas of the business, and they became full-time employees.

At some point, one of our developers left.

So now it is me, Lizzie, our lead developer, a jr developer and two assistants who help with sales and chores.

I love it so much more than being on my own. It wouldn't even be necessary for me to program anymore, but I do when I want something done or it just makes sense for me to do it or I'm just trying to make the business better. My point is that my lead developer is so good, I can trust him to do a great job on any idea I have. It took a while to get to that point, but now that it's happening, it's awesome.

Lizzie now does so much on the business end (and has taken over most of my emailing) that I have freed up a ton of my time.

I now get to look at the bigger picture, figure out how to expand the business, manage people and have fun.

I think by far my favorite part about all this, is that now all I have to do is have an idea and I know that I have a team behind me that can make that idea happen. Also, I can go on vacation.

It seems to me that if you are making $2M, then a couple of really good employees at $125,000 should be able to help you bring in more money than they will cost.

I hope my story helps you. I think it worked out really well for me. I didn't really have a plan, I just got lucky in many ways, but I was also always paying attention and I trusted myself to know when someone was right to work with and when someone was not right to work with. In general, if I had to give advice from my personal experience, it would be to hire the best people you can. Make sure they are remarkable. And get rid of people that you have any issues with or aren't that good.

Think about what specific aspects of the business generate profits and where your costs lie. To rapidly expand, you'll want a multiplier that greatly increases profits or drastically cuts costs.

As a thought exercise, think about what you'd need to do to double or triple your sales. A bigger marketing budget? Institutional clients? More staff? Content? The details will depend on the specific nature of your business. Once you have one or more scenarios laid out, work backwards and figure out what's required to get there. The result will give you a good idea of what investments to make to grow your business.

Hugely impressed by what you're doing. Congratulations! If I were you, I'd start by hiring an assistant to help me deal with distractions. Maybe even a junior accountant / clerk to help manage payments, bills and some basic finances. So I could focus more on the core-business.

I'd love to be in a position to work with/learn from someone that's been as succesful as you in building a more or less solo business.

You didn't share a whole lot regarding which area/niche you target in your eLearning business (I'm guessing that it doesn't cover a wide variety of topics, unless you're a superstar that has a whole bunch of knowledge across a wide variety of topics :-).

But if I were in your shoes and looking to expand it would probably make sense to want to try and recreate the same success as the existing eLearning products in a new niche/area so you might need to recruit someone with a different specialty that has the requisite knowledge.

Another strategy I've seen used (this was about 10 years ago when I was fresh out of college and looking into how I could make money online), mainly by folks that were selling products in the "how to make money online" category, was the cross-selling between different groups of these people. Essentially, if you had purchased from one of them, it wouldn't take too long until you started getting emails from the one you had purchased from that mentioned a product from "one of their good friends" that sounded very good too and it was difficult to pass up wanting to purchase the other products (I definitely spent way too much during this period on these sorts of things before I realized how much money I was spending and realized I really needed to tone it down). It was effective though, and was more of a collaboration between similar eLearning companies selling products in this cross-selling fashion.

From the pure employee side, it looks like ZenPayroll has changed their name to Gusto (https://gusto.com/), but I think they have a pretty good offering for a small business wanting to expand and hire employees by helping to simplify the tax parts of things for you.

You also didn't mention if you were operating as a sole proprietorship or already as some sort of safer Corporation/LLC organization, which you would want to consider doing as well to help protect yourself, particularly if you would be hiring employees.

I myself have wondered / thought about the same problem you yourself have asked here though...I've just never been successful enough to actually be able to act on it (my little software business only makes about $100/sales or so per month so not enough to hire anybody unfortunately :-). How do small companies deal with this stuff? I think in a lot of ways they deal with it by having someone that's experienced with all of the "paperwork" side of things. My uncle for example ran a small business with his son painting cars, and neither was particularly knowledgeable about any of the business side...they just knew how to paint cars. My aunt on the other hand had experience with that sort of paperwork and taking care of it so she "abstracted" that away from having to deal with it. You'd likely need someone similar to help with those sorts of things (though again, Gusto may help with quite a bit of it, at least with some of the regular stuff related to taxes if their product hasn't changed much from the ZenPayroll days).

I wish you the best of luck, and if you ever want an eager, young fellow to work with feel free to contact me (email's in my profile :-)!

Here are a few tips that will help you.

1st do not hire anyone unless you are 100% sure you can define a full time position for them. Outsource as much as you can until you feel it's cheaper to bring some one in house than to hire a consultant. $2 million seems like a lot but it's amazing how fast that gets spent once you get others involved.

2nd spend the time to define what you want your business to look like in five years. Define every year and set goals on how to get there.

Create a business plan. This will force you to look at your business more broadly. There are plenty of books that will show you how to start. A good question that will be answered is whether your business can grow or if it's just a small niche.

Educate yourself, if you don't, others will be happy to tell you what to do and how to spend your money. But don't expect them to have your best interest in mind.

Your 1st goal as a business owner is to make yourself obsolete. You can be an employee but the company can not be dependent on you. Once you do that then you can guide the company's future. Delegating will be extremely hard but if you hire right then there should not be any question as to whether it's possible.

Going from 1 person to many is a great change. Your goal is to get everyone to work towards the same goal. Make sure everyone knows what that is. Communicate, communicate and make sure you communicate. Getting your vision from your head to someone else's is hard.

Lastly, don't be in a hurry to spend money. It's funny how it works. If you can define a viable business then people will be happy to give you money to keep it going. There's the other side too. Don't be cheap. Cheapness can do more harm than good. It's a balance. You'll have to find it.

Good luck!

If it's not broke, don't fix it.

I think it'd be important to define what do you need to organize (because an organization is about, well, organizing), and how it will contribute, where it will contribute.

Happy to chat more. Email in profile.

Would you be willing to license your platform to an overseas franchisee?

As another solopreneur, who is doing a fraction of what you are doing... I would love to talk to you about how to get to something even close to the position that you're in now.

I want to grow my business, and be even a fraction of that successful. Care to talk?

There are some interviews on IndieHackers.com from people who've been in situations that are semi-similar to yours. Happy to make an intro to any of the interviewees you'd like to talk to.

I am currently doing the exact same thing. Started to employ freelancers and half-time people to do the things I do. Thought I could handle the stress and just figure things out while I go. Well I could not. Revenue went up but profit went down. Was still a good experience, because it showed me, that it can be done and what I have to do to make it work. So I took a step back and I am now documenting. Every. Single. Thing.

You cannot imagine how people find ways to do stuff differently than a sane person/you would do it. Might sound like a small thing, but the final drop for me was, when I asked for the results as a zip archive and got a .7z file starting with two dashes (--for myname.7z). I decided, my time is not well spent when I have to look up how to handle files like that in bash. How can you even possibly come up with something like that? The guy must have been very talented at QA, because he clearly knew how to produce edge cases.

Another thing I do not want to do a single time again is setting up environments. Even if you use something like Vagrant, this is such a huge pain in the ass, because even these technologies do not just work. Yeah, they work the same on the same version of OS X or Ubuntu, but the real fun begins, when helping over the internet to set it up on an OS you are not on yourself. I will not do this again. I am not sure on how to solve this yet, I am currently leaning to just defining the environment and just require it, require them to work over SSH or literally send a laptop out. This is so much pain. "That's it"-story here was a guy on a test project, who did not manage to set up Ioncube Loader, because he had the wrong PHP version and literally manipulated a screenshot of phpinfo(). I did not know whether I wanted to laugh or cry.

So now I document all the things. I have a huge collection of linters and checkers bookmarked. I write style guides for every product, with even the smallest things defined ("how to name a file"). For every task there should be a checklist. Enterprises call these "standard operating procedures". I have a flow chart on how to spend my own time, starting with "Is there a new email in the inbox?" all the way down to questions that handle bankruptcy.

What I do not have yet is a really good way to make these documents accessible. There are SaaSs out there (process.st, sweetprocess.com), but for me these did not cover all the cases. I used Google Forms a bit, but ultimately I want a nice platform to handle everything together so user authentication etc. is unified. My current plan is to just use Gravity Forms and WP Knowledgebase. I think ultimately I will end up with something custom done, but until then done is better than perfect.

What many people here already recommended and I cannot stress enough is this: You do not want employees. The huge benefit of software or consultants over employees are obviously no running costs and the ability to just require perfect results. Request what you want, attach your style guides and SOPs to the contract/code, deadline, contractual penalty and done. So first write your processes down, after that: standard software > custom software > freelancers > employees.

Also what other people already have said: Start from the bottom. You do not want sales automated, first you just do not want obvious false positives inside the inbox either trough automated filters or through a person with a process to specify if you actually do what is requested in the email. Now you are left with actually relevant emails, what would be the next step? Huge benefit of this is obviously, that you can use cheap workers. Now write a process on how to find them. Then write a process on how to write that process.

At the end, hire a COO to execute the top level process. Ideally he or she should now not be running your company, but creating companies similar to yours. Of course, this probably will not happen, there will always be fires to extinguish.

Regarding your specific questions a...

Seeing from your earlier post about a year ago when you seemed to be dealing with a burnout, I would recommend getting a co-founder or someone experienced who can guide you.

Handing out some responsibilities is not bad, it's what happens when you grow. It will help you to scale and grow more easily with less stress.

Good luck!

That's awesome and glad to hear you're doing well. I think you have a couple of options:

1/ Keep running it by yourself. 2/ Hire an assistant to take care of time-consuming small tasks. 3/ You could always talk to a couple of larger competitors and see if they're interested in buying you out.