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

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.

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.

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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.

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!

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.

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.

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.

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.

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.

(First time on this site, someone sent me this thread)

About 16 years ago, I was in a kinda similar place to you - making a lot of money but ambitious and wanted to grow grow grow. Not a tech biz but very information centered.

Very long story short, while it was far from easy or an uninterrupted "up and go the right" path I was fortunate enough to survive my gazillion mistakes and we currently have about 150 staff in 7 countries. I don't have any investors, partners, or significant debt. I spend about 95+% working "on" my business vs. "in" it.

It sounds like you're a good guy and perhaps my input can help you think through your options. If you drop me a note we can do a brief call and see if the chemistry is a fit. I've never done any coaching or mentoring outside my own organization before but I wish I had had access to a resource like the 2016 me along the way so it stands to reason some of my takeaways from my journey could be of value to you.

Best wishes for continued success.

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.

We started with a combination of a few developers (indeed we started with one!) and one QA or tester to check the work done by developers. Even if the developers are excellent, having QA in place unload work from the developers, increase the delivery quality, and save you a lot of time. I think this is a basic framework. Setup development, testing and/or staging, and production environments, so if you don't want to give a lot of control, at least you can deploy and configure stuff once it is working in the staging phase and be more confident about a new release or configuration.

We always hired for a 30-hour work week, obviously we want people who will stay until the critical problems are solved but we try to keep longer hours work at a bare minimum. Our first hires were oriented to some specific technology plus a flexibility to use technologies outside their comfort zone. For example, a C/C++ expert who could do part of the work in Visual Basic because it was the right technology for the project, or people who can move from Node to Python easily, and at the end of the day are not mad if they choose React or Angular.

Like everyone else, we want to hire the best and trustworthy professionals via people we already worked with. If we can't hire the best we look for people with an excellent predisposition, a more than average intelligence, and very good communication. Communication is key, if they found a problem that is really difficult to solve we want to know this as soon as possible and will discuss it with part of the team to help as a group. We don't like heroes who engage in very difficult problems without giving us a warning.

We have a few remote employees who really know how to work remotely. We would never start growing with remote employees, except if you know them very well and can be on-site too.

Beyond this, our hiring process is simple and mainly based on experience/work-portfolio. No puzzles.

Disclaimer: Since my business is not based in US there can be many differences in the way we handle similar issues.

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.

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.

https://www.saastr.com/what-a-vp-sales-actually-does-where-t...

What is the biggest problem or pain point you have? Put another way, what activity consumes a lot of your time that someone else could just as well as you could (or better)?

Dealing with tech is the easy part, it's the people that will get you.

Sounds simple but.. when you hire a technical guy; hire/keep the ones that are smarter than you. This allows you to let it go. If you thrust them to doing a better job than you would, its easyer to not get in their way.

On HR vs core employee: if you have fulltime work for a core employee, get one asap. This frees up the time you need to build your bussiness instead.

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

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.

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.

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.

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!

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

If you are making that kind of money solo, you are a small minority. I would stay where you are. If it's not broken, 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.

Contact info is in my profile.

1. Be super clear on your why: You must start by clarifying why are you doing what you are doing; why are you in an eLearning business. You are making good money and from what I read in some of your replies you are doing well fro yourself, so what drives you to wake up every day and go to work, what brings you joy. Why is this so important, because it's the key to everything else, for example, if you want to hire people for the long term, the must believe what you believe, if you want your business to grow beyond you, ie must be driven by a clear purpose (your why) Your why is a great for rapid decision-making, which speeds up things in your business, in hiring, in growing your customer base...etc

2. Be super clear on your goals: You have a successful business as it is, and expanding it is not going to be easy, it is more work for you, so why are doing that, what will things look like when your effort to expand your business are successful and you get everything you want, just the way you want it. This will help you clarify where you are heading and so you will be able to choose your the steps and measure your progress towards achieving your goals.

3. Start with 20%: In every business there is 20% of tasks and things to be done that are repetitive, mundane, laborious, maybe even boring for you. Even if you love what you do, there will still be things you like more than others. Start finding people to do those tasks. People who believe what you believe and love doing these tasks. This is a very safe starting point since these are not the major tasks that have major impact on your business.

4. Hire for personality more than skill: This may sound strange, but the top team members that I've every worked with and that outperformed everyone else were the ones that had the least skill but the biggest appetite for learning and growth. They were like a sponge, were willing to learn, and most importantly, they were not affected by the way things are done out in the world. As a one man show you may be doing things differently than how things are done in other big companies or the regular practices in other businesses, so you may want people that are willing to learn your way of doing things. People who are used to doing things in a certain way will drive you crazy trying to unlearn how they do things, while people who have less experience and more appetite for learning, are more open to learning your way. This is not to say that people with a lot of experience are bad, in fact if you can find great people with great experience, that would be ideal, as long as they are open to learning, willing to work with you and love to grow.

5. Continue your journey to 80%: Now that you have handed over 20% of the work to new team members. The ideal goal I suggest is to continue hand over tasks to existing and new team members until you reach 80% of your tasks delegated and handed over, that way you are only doing 20% of the work. You do thins gradually 30%, 40%, 50%...etc Keep identifying the tasks that are repetitive, the tasks that give you the least pleasure and joy, and keep finding people to do it. until you are left with only 20% of the work you originally used to handle, this 20% is the most important work that only you can do, it's the heart and soul of your business and your brand, the reason why people come to you and work with you. So you are still in full control of what matters most in your business.

6. Ensure Continuity with Processes: One of the things that will increase the value of your business and make it thrive no matter what happens to you, is to make it a process driven business. Make sure the people you hire spend 80% of their time doing the work, and 20% on enhancing and documenting how it's done. This is very different than reporting to you and increasing paperwork, that is not necessary. This is about them learning to do it better, not just from you, but on their own, and instead of just doing it, they create processes that describe how they do it now, and they keep updating the process as it evolves. The documentation needs to be clear to the point that they can easily hand it over to anyone on the team. This is crucial as this means that if they leave or anything happens, you can easily hire for the same position without having to lose the intelligence that has gone into teaching that person and the learning they developed by doing and enhancing their work. Documenting the process of how they do their work, will ensure that they learn more and advance in their work.

7. Never delegate leadership, develop leaders: you are the only person that is responsible for the totality of your business, so you must do the above yourself, do not delegate your responsibility, this is your business, you lead it, don't leave leadership to anyone else. You must develop your people to become leaders, by giving them the space to lead and working with them, helping them, supporting them, but neve hand them leadership, that is not how it works. By following the steps above, and by creating an environment where people are given the space to shine, you will see your team rising up to the tasks they are given and show up as leaders. One of the other ways people can show you what kind of leaders they are is to have them help you choose the new people, train them, and support them, even if they have different tasks and different roles, they are still a team and that dynamic will help you discover what kind of people they are.

8. Security and protection: While you can never fully protect anything, you can take conscious steps to make sure your business and the assets of your business (domains, sites...etc) are secure. Make sure you structure your contracts with your team to include nondisclosures and protection of business secrets. Include no competition clauses so they can't leave and take your clients or work for a competitor for at least 6-12 months. Finally, never give passwords away to give people access, use password protection services like LastPass to give people access to things without sharing your passwords. Also you can request form your service providers certain accesses to team members, that way you still have admin rights and you have the ability to add or remove people without giving access to the main account.

9. Be the role model, Keep on learning and growing: There are many mentors, coaches, business experts out there that you can work with to continue to grow and learn how to run your business better, explore that. And there are always brilliant business books that can expand your thinking and ability to lead. Here are a few I recommend: Anything for Jim Collins, especially Great By Choice Anything Seth Godin, especially Tribes Anything Simon Sinek, especially Start With Why and Leaders Eat Last Anything Charles Duhigg, especially The Power of Habit

I trust this is clear and helpful

Wish you all the best, and please reach out if you think there more I can help you with

he does a 1 hour call a week now

In terms of what you should do, it's hard to know without the specifics of what your business does, who you are, what you are good at, how your business will grow, etc.

I think there are some general thoughts that may help:

1. Early on, overpivot on people you can trust who happen to be good, not people you can't trust but who are great. Also don't hire your friends. Most people want to hire the best people they can but I've found that loyalty, work ethic, and trust are more important for the first or second people you hire. But hiring friends or family can often blow up so avoid that.

2. Figuring out how to hire people is hard. Managing employees is hard. Keep the stakes low initially and then figure out how to hand off ownership of more core things after you feel like you have a good sense for how to hire and who to hire. Start with something you know really well that is not going to lead your business to fail if you hire the wrong person. Hiring someone to do work you know well lets evaluate the quality of someone's work. Putting them in a role where they aren't working on something critical minimizes your risk. For example, if you are doing all of your customer support right now hire an Android developer if you know Android really well to add a new feature to your app. Don't hire an engineer to work on your payment system if you don't know that part of your stack or if you can't afford for your payment system to go down.

3. There is no comprehensive resource because every business is different so you will have to spend a lot of time reading. Read through everything related to business, entrepreneurship, hiring, scaling a business, etc. on Quora. Ask questions there and see who responds. Find the courses similar to what you want to learn at top business or engineering management schools (Stanford, Harvard, MIT) and look at their curricula. Read everything in their curricula. Read this post I wrote several years ago about the dynamics in the education space in the US to make sure you don't fall in to the trap that many education entrepreneurs do around thinking that your business can actually scale far beyond where you are today: https://avichal.wordpress.com/2011/10/07/why-education-start... Google searching will get you quite far too: https://www.google.com/#q=hire+first+employee+startup

4. Find successful people who have built a business in your space that is 10x bigger than yours, 100x bigger than yours, and if possible 1000x bigger than yours. Email these people and ask for advice. See which of them you click with. Ask them all of the questions you have and see where a relationship develops. Ask them for the best resources thy know about related to your business or how to scale a business. For example, I tell a lot of entrepreneurs to read High Output Management by Andy Grove to see how an experienced manager and executive thinks about running a large organization. You are not yet running a large organization but you will learn a lot and can work backwards to lessons that are relevant for your business today. In general, you will be surprised at how often successful people will actually help out. It's entirely possible (and likely) the woman that has a $200M business today was in your shoes a just few years ago and is willing to help.

5. Find successful people that you respect outside of your space and do the same as in #4. Consider raising investment from experienced people who can help you. Applying to YCombinator is a good option if you don't even know where to start.

6. See if you can find people that want to learn what you've done and could help you. For example, there are probably people who want to learn what you've done to bootstrap your business but who are running a small part of a very large company. These middle managers could teach you how to build an org and you could teach them how to start their own business.

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 around access management etc.:

You typically want to find out how enterprises do these things or what the industry standard is and then go from there. So for example you would write down a process on how to set up a server, now look what tools are used to automate this. The answer is Chef or Puppet. Are there simpler/easier tools suited for smaller companies? Yes, Ansible. Bingo, rewrite the process as an Ansible script/buy one, you have now automated the process.

With access management, the keywords are key-based authentication, LDAP, a contract of what evil will come on these who abuse their trust, a process to onboard, a process to fire (where do I need to restrict access?).

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 :-)!