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Ask HN: I am doing $2M annually as a solopreneur and need your help
122 points by techcorner on Aug 27, 2016 | hide | past | web | favorite | 88 comments
I work as a sole founder with little work outsourced and an employee to help with chores. My technical background coupled with marketing exposure I am able to enjoy awesome profit margins in my eLearning business. I now plan to expand my offerings and hence team but have no clue where to start. I don't want a co-founder as such. Right from the smallest of technicalities like giving control of my domains, server, sites to employees scares me. Then whom should I hire first, a core employee or a HR person? I have never dealt with such stuff and no clue how to proceed. How do small companies deals with such issues? Is there any exhaustive resource/course/book/video/case-study which lays down a process to take a 1 man company to a 'n' person organization? Sorry for my naivety. Would love to get answers from the super awesome HN community.



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.


Thanks for your inputs. Nice House. Check. Nice Car. Check. Happily Married. Check.

Just keep doing what you are doing for as long as you can and take the cash out.

I am quite a super ambitious guy and I don't wish to keep all my eggs-in-one basket. Though am doing good for several years but we can never be sure of things when technology changes so abruptly. I feel if I am able to expand, I can multiply my finances and the value that I can give back to society many folds.

I sincerely thank you for putting in your time to answer my question but my original question remains :).


OK well all I urge is that you continue in your current configuration until you never need to work another day in your life. THEN do the company thing.

You will regret it beyond all understanding if you take this incredible position you are in and within five years turn it into a financial disaster back to square one.

Frankly you are undervaluing what you have achieved and underestimating how hard the task is to tenfold that.

In ten years of continuing in your current configuration it sound like you could take home more than $1,000,000 per year AFTER TAX. A "company" can easily run for ten years and not have yielded that much money either through revenue or acquisition.


It's painful how much I agree.


The problem is that if success comes too easily and/or too early then it is undervalued.

I made a big pile of cash very early in my career and thinking that such big piles of cash were easy to make, promptly wasted it on "starting a company". I certainly gained value from that money though. The value I gained is the wisdom that I imparted in the top level suggests to the OP.

Cash never came as easy again.

The OP doesn't realise that he has attained one of the possible levels of startup holy grail nirvana of success - the incrediprofitable one man company.


The problem is that if success comes too easily and/or too early then it is undervalued.

I am sorry if I made that impression. It was never an easy thing. I have had my fair share of all-nighters and even I do those now at times. I had to self-learn, un-learn several things after leaving a comfortable job several years ago. It was (and still) not at all an easy task. As a quote goes It took me 10 years to become an overnight success


My point is not about how you got there. My point is that you undervalue what you have.

Perhaps the most important point, and one not made here elsewhere, is that merely the fact of starting to create a company will impact your existing revenue stream. You will instantly become distracted by "working on the company", and whatever your current magic formula is will suffer and revenue will go down. The moment you start to "make a company" your magic formula will get less and less magic until soon you've got 10 employees, a lease on an office, taxes, problems, a sales team, politics, accountants, hiring and recruiting, and then you need to feed that beast with ever increasing numbers, and you'll stop taking all that juicy cash for yourself because you'll be "investing it in the company", which is to say "spending it/getting rid of it". Your magic formula will be gone and you'll be just another ordinary company.

And if it did take ten years to get to this point then why the heck are you in such a damn hurry to change your situation.

I think what you should do is change the way you see your current position.

Currently you are WILDLY SUCCESSFUL. You seem desperate to risk that for what - greater success?

What you propose makes no sense. Just keep doing what you are doing. Keep raking cash off the table and start to think to yourself "wow, I'm one of the most successful people in business".

The problem for you is you are addicted to "entrepreneur porn" - you are reading about all these other people who run REAL companies, who EMPLOY people, have OFFICES, and INVESTORS and IPOs. All that stuff is nowhere near as valuable as it is made out to be. You have done the most incredible thing which is to pull in huge amounts of cash with none of that crap. Wow. But you seem to feel that it's not enough success. Readjust the way you see your achievements to date and readjust what the real value is of "having a company".


This is one of the best comment threads I've ever read on HN, thank you.


Not to mention he is in education - a universally moral category. This is startup nirvana if I ever saw it. I'm sure there are famous billionaires who would trade places with him if they could


Not to mention he is in education - a universally moral category

I sincerely hope that is not to be taken as sarcasm?

This is startup nirvana if I ever saw it. I'm sure there are famous billionaires who would trade places with him if they could

Can you be more detailed please?


I'm pretty sure majani simply meant that your helping people learn is a Good Thing.

So you are doing well by doing good.


> "entrepreneur porn"

Maybe I've got a fetish--what he's doing is the porn to me!


Don't think hoodoof disputes your hard work for many years. Your current situation could potentially be a gold mine which sets you up for life. I guess he is arguing not to increase the risk. Despite all the hard work you might not be able to scale it in the same manner.


I guess it depends on what you are trying to accomplish. Many people start a business because they have a purpose or mission they are trying to accomplish and they can't get there remaining small.

That said, I'm inclined to agree that granting yourself and family financial independence gives you a lot of freedom and flexibility to do anything you want at that point.


Please take this advice


Hoodoofs advice is sound. You are about to find out that every entrepreneur wants to be you: making a lot of money WITHOUT personnel, co-founders and shareholders.

Your financial security should be your first and foremost ambition. Only after you have enough money to never need to work again, think about expanding or restarting.


I couldn't agree more.

There's, I guarantee, MILLIONS of things to figure out for making a "company" which techcorner thought of. Taxes, lawsuits, security, employment laws, facilities: you name it. Yes, true, by bringing in more people, growth _is_ possible, but there's also a lot more risk involved. Usually, you add more people because it is the ONLY way to get to where you need to go.

While there's nothing wrong with teamwork, it _can_ go horribly wrong. The corpses of failed tech startups litter the pages of past TechCrunch articles. Don't become one of them, techcorner.


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.


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!


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.


But you need someone who you can trust, who you feel like is smarter than you at some useful set of skills.

Tell me a recipe to hire such a guy. Please.

Someone who is as passionate as you are about what you do

hmmm this is probably easier said than done.


The recipe? It's not easy. It's all easier said than done.

But you already built a two-million-dollar-a-year business. Did you expect this to get easier? :)

It's probably not too hard to find someone who is better than you at server administration, and it may not be too difficult finding someone who is passionate about what you do. Finding someone who fits both categories is what makes it difficult.

There's a lot you can do to start looking. Define the job, all the responsibilities, technical requirements, etc. Post ads or fish around in your network. Ask who knows smart people. Make sure you're clear about what you do and that you're looking for someone with an interest in it.

It is possible to find someone who is the kind of geek who likes to get paid to solve the technical problems and will do a great job without caring about your mission - it's up to you whether or not that's an acceptable hire at this stage. (IMO it's usually not a good idea with the first few employees, but once you have more, it's okay as long as they're still a culture fit in other ways.)

If you find someone who is passionate and hungry but doesn't have all the skills, this is potentially a very good hire. Hire and train them, and eventually they'll get better than you at their area of expertise.

Most technical people won't have the EXACT experience you're looking for, so you have to think about gauging them by their potential to learn - look at past projects, ask questions that test their curiosity and ability to explain things, try explaining a new idea to them and see how quickly they pick it up and run with it.

This is one of my favorite parts of building a startup. I just quit my job to start one and I'm not at the phase of hiring yet (still doing everything myself, nothing to release yet), but I'm REALLY looking forward to it, assuming things go well enough to get there.


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.


I really don't want to criticize the OP, but as an observation, the question reveals such a deep level of naivety about how to run a company that it bodes very poorly for the transition of this company to same-but-multiple-time-bigger-and-more-profitable.


Yes I am aware of my shortcomings and I did qualify that already in my original question.

I am a fast learner and open to learning - given a good source.


Step One: talk to a local temp-to-perm agency about computer literate clerical staff or a personal assistant. This lets you defer ALL the HR/payroll/tax issues until much later.

[Also: please put contact info in your https://news.ycombinator.com/user?id=techcorner HN profile]


If you can successfully outsource a non-core function, then do so. HR is one of those things that can be successfully outsourced particularly at the small scale.

The only maybe gotcha with outsourcing the HR function is that, while you can outsource the routine tasks (issuing payslips), you can not outsource to an outside firm the legal obligations surrounding employee contracts, employment law, obligations to pay correct payroll taxes, etc.

If you go the route of outsourcing HR, you may wish to consider investing a bit in HR consulting with the aim of educating yourself about employment law in your legal jurisdiction.


I would like to thank each and everyone of you who took time for your valuable answers. However, with due respect, I see that most of the people are over-fixated on why I should not expand. I am already in an extremely comfortable position when it comes to money. All little necessities of life like insurances, house, car have been already being taken care of. The place where I come from even if I stop working today, I can live comfortably for next 10 years. Except a couple, most of the answers are telling me why it is not a good idea to expand. I understand their sentiments but this was not my original question. To give you more details - This is an eLearning subscription model. Other than questions in my OP, hiring, managing, trusting emp with sensitive info, finding very high quality content creators remains as one of my biggest challenges. I am not from any of the developed countries. I dominate my current niche but looking to expand into other related niches where I see a good competition.


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.


Thanks for chiming in. How do you keep their motivation going especially for a talented developer? Don't they just want to leave a small startup and want to work for biggies out there?


Well, right now, my whole company (plus wives and girlfriends) and I are on our way to burning man.

We also live in Aspen, and my lead programer is a huge skier, so it is a unique and fun opportunity for him to ski and live in Aspen.

Also, I pay them competitively and give them a profit share.

We have a lot of fun and have a lot of fun at work trying to grow the business too, because it's good for everyone.


The profit sharing is what would hook me and, I'm sure, plenty of other entrepreneur-minded programmers. That's something you can do at a small company that a big company won't do. It also gives employees a since of ownership, and aligns their incentives with the company's. I believe Wufoo did something similar with great success.


Right, anything else in such a people-dependent industry is capitalist bullshit. The company consists of the people in it, they deserve a direct share in the profits.


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.


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.


Hi Techcorner,

(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.


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.


We scaled a 2 men (my partner and me) 15 year old profitable (no investors) company to 12 people and we never were in a market position to scale much more but we are good (much better than the average) hiring.

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.


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.


Yes, it works on a subscription model and I pretty much dominate my micro niche. I am looking forward to rine-repeat this model to other micro niches in my parent niche.


Thanks for confirming. Any chance you would share your site? Or does the fact that it is a micro niche mean you worry about competitors starting up and can't promote it more widely?


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.


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.


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.


+1 on this. Before scaling your team, scale yourself.

You can hire remote assistants extremely cheaply – I've had success with Zirtual and Upwork.


You may just want to look at hiring an assistant first. Some one that can take on the easy time consuming tasks. Let them build trust with you before you "hand over any keys" also I wouldn't hand everything over to one person. If you want someone with more experience then find someone with traits and interests exactly opposite of the things you want to do. here's a pretty good article on hiring a vp of sales:

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


> Then whom should I hire first, a core employee or a HR person?

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)?


Very high quality content creation. Difficult to find people who can provide content at quality which I aspire for.


Do you mean that you need instructors or people to take existing material and get it into your platform?


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.


Thanks. Beautiful site. Looks interesting.


Leave your current company alone, and safe, and use a years worth of the profits to start something new. Keep doing that until second thing is making as much money as the first, then start changing your old company around. Best of both worlds, and you can still follow everyone's wonderful advice. Be safe man, don't goof up that absolute boon you are sitting in the middle of. Paramahamsa Hariharananda - "Shirk not opportunity, for opportunity may not come again."


creating quality content is not easy but you have a good start. I think you should adopt a publisher model, you already have captive audience in terms of paying customers for your niche. You can find out what else would be relevant to your customers and design a curriculum around it, no content, just the table of content for your next course. You might as well publish it to your website in coming soon section and give early bird discount(which would guarantee paying customer and fund the development of course.) if you don't get any customers don't go further in developing that course. Outsource the research on material for your TOC to virtual assistants, they will be responsible for curating and providing you the quality material. Once you have all these you can as well hire an intern with good communication skills who is interested in this course (say machine learning) but may not have the knowledge. Groom him and ask him to come up with writeup for your TOC. Hier high paid thought leader for this course as identified by your assistants while doing the research and let him be the editor for the content. RESIST any attempt to do it yourself if intern/assistants are not able to do it the way you want, just be patient. Rinse and repeat and send me 1M$ that you make from your next niche ;-)


I worked for a company years ago that was in the same situation that you are in now. I was the first employee brought in to assist with the more day to day operations of the business. Things went well for a while. We added on more staff and I moved up and that's when I started to see the problems with the founder. His lack of management skills began to take its toll and the company was dead in the water six months later.

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


Congrats to your success. I think it starts with your objectives. Do you have other product ideas you want to get off the ground? Do you want to stop wearing a few hats (like marketing, finance customer service, etc). Where do you see the business in 2,4, and 8 years? I am currently in a great position leading product for a healthcare technology company and I have asked myself the same questions. A hiring plan fell out of that discussion and has so far been very successful.


Do you have other product ideas you want to get off the ground? I have a list of ideas sitting in my To-Do. I am limited by my time. Wish I can hire some smart folks to execute them. <- Hiring smarter folks than the owner is the sentiment echoed in several comments in this post. How to do that is what we all need. Share profit percentage? Yes, but how much? on what basis?


Right from the smallest of technicalities like giving control of my domains, server, sites to employees scares me.

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.


hire/keep the ones that are smarter than you. How? Why would they join a small company?


> Why would they join a small company?

Once the basic needs are met, many smart and talented people look for internal motivation. It doesn't matter if it is a small or a large company, as long as they are happy and satisfied. According to Daniel Pink's theory of motivation [0], there are 3 aspects of intrinsic motivation: 1. Autonomy - trust them, don't micromanage, let them take decisions 2. Mastery - allow them to get better and acquire skills 3. Purpose - give them a meaningful purpose and sell them your vision

Internal motivation may mean differently for different individuals, but I believe the above three aspects cover the most of it.

[0] https://en.wikipedia.org/wiki/Drive:_The_Surprising_Truth_Ab...


There are lots of reasons for choosing a small company over large ones: interest in the field, involvement in decision making, maybe more technical freedom, less bureaucracy ... I would say it depends more on the company itself than its size


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

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


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.


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.


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.


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!


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?


First, how do companies deal with the issues you mention? Answer: learn to let go and trust the people you hire.

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.


OP, is there any chance that you have some time to impart your wisdom and mentoring a person(me) that aspire to achieve something similar. It would be awesome if i could learn what you learned in being an overnight(10yrs journey) success.


Have been doing so within my friends/family. Will consider mentoring on a larger scale as and when I can get time.


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.


In case you are looking for associates in the EU, drop me a mail. I'll share LinkedIn if you wish, and we can discuss matters privately. @gmail.com prefixed by my username.


I've seen a few friends go down this path, happy to introduce you if you're interested.

Contact info is in my profile.


I spent 25 years running successful small businesses and moving them from 1 man shows to becoming team based businesses. Here is the process I used successfully time after time in my business and helping other businesses.

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


This was one of the better responses on this thread. Couldn't find your contact details. Please reach out to me through email mentioned on my profile.


Glad you found the reply helpful, will reach out :)


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


a friend was in a similar situation. he has a team now and a CTO to handle day to day technical issues.

he does a 1 hour call a week now


Contact me at matthew349hall@hotmail.com


I'm going to disagree with a lot of the sentiment here. I think it's rare to find a business that really truly works and you may have found the beginnings of one. Be ambitious. Figure out how to scale this 100x.

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.


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 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?).


I think this applies to hiring employees as well, no?

You can't hire hire someone and expect them to do the job unless they have a well written spec and there's extensive documentation on setting up a dev environment, deploy process, etc.


Sure, but you still have to pay them, if they anyway manage to screw it up.


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 :-)!


I'm guessing that it doesn't cover a wide variety of topics

Your guess is spot-on. That's why the need to hire talented folks and seeking suggestions here.


I recommend reading The EMyth and to a lesser extent the 4 hour week.


ok thanks. This is the 2nd rec for EMyth today. Will definitely put it in my reading list.


I'd put it at the top of your list, considering it touches on exactly what you're about to endure.




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