Ask HN: As a first-time solopreneur how would you go about hiring the first team

[_448]

I am interested in understanding how would a solo tech founder hire the initial sales, marketing, operations, cyber security and DevOps team members?

Assuming that I don't know anything about or have zero experience in the skill-sets I am hiring for, how does one start? What questions to ask, what to look for and where to look for the talent?

[louison11]

Something obvious I didn't understand at first: the earlier stage you are, the smarter the people you need.

They need to be autonomous, flexible, but above all brilliant at what they do.

If you get "average" employees who just wants to follow the specs and receive their salary, they will most likely cost you more to manage than they will create value.

In early stages, you're probably still trying to answer complex questions - and you need people who have the capacity to think outside the box to do so...

As you grow, you can start tolerating people who "think less" and just do what they're asked. You'll have managers to manage them.

In other words, the type of people you need at this stage are the type who could be almost be startup founders themselves. ;-) My 2 cents.

[RamblingCTO]

Totally agree with that. This will play into your mental health as well. The more weight other people can carry, the less you have to do. Don't underestimate having to feed the brains of 10 people constantly when they can't/won't think for themselves.

[pleoxy]

The word you are looking for is responsible.

Someone who will take burdens from you and go handle them themselves and don't need to be cajoled, directed every step, motivated, managed, etc.

There is crossover with smart, but that's just a nice to have - responsible is the primary attribute you need here.

Plenty of smart or even brilliant and still lazy people out there that will not fit here.

[Hasz]

The caveat being… brilliance will cost you. If you incentivize them to care deeply and solve your hard problems, and they have the capacity to do so, they will. But if you don’t, they’re not just going to toil unnecessarily for an incommensurate reward.

[atomicnumber3]

Do you reward these people with more than a fraction of a percent of equity? As someone who likes WLB enough, isn't enough of a gambler to take a 0.001% chance of being a millionaire over a 25-50% chance of getting a nice 6 figure payout from a more established startup, and has too many kids to boot, I never bothered looking at a company that didn't have a health insurance plan and a 401k match. But when I learned it was common for a founding engineer to get like half a percent of the company, I was appalled. I'd rather just start my own startup and roll the dice there if I'm still going to have to build the whole damn thing just for a fraction of a percent in equity.

It seems super weird that you'd literally be in the trenches with 1-2 other people who each have as much equity as 50-100 of you.

Otherwise, I mean, why should someone brilliant work for you instead of a company with much better odds of success?

Clearly, companies do hire founding engineers at these rates so maybe I'm the crazy one. But it just seems wild to me.

[codegeek]

"the type of people you need at this stage are the type who could be almost be startup founders themselves"

Pretty much. I run a bootstrapped SAAS and built a small team over the years. I havae made so many mistakes when hiring the early employees. So many. The biggest mistake: Hire someone who will be a good fit in a larger team/corporate where they have structure and are told what to do. Do not hire those people as your early employees no matter where they come from or how smart they are in general.

You need people who are "almost" entrepreneurial but cannot do their own thing. They love to own things, have autonomy and can wear multiple hats. They are willing to experiment with you and most importantly, move the needle. Very difficult to find especially when you are a nothing startup.

[Woshiwuja]

Unless you are a startup which deals with highly complicated technologies and algorithms you don't need the smartest people around.

[repelsteeltje]

Can't speak from experience, but my recommendation would be to never hire someone to do work you've not done yourself. (I believe Joel Spolsky mentions this.)

So for instance try doing marketing yourself for a month. One benefit: you may discover you're good at it and don't need to hire someone, or hire someone freelance or part-time. The more important benefit: when you're interviewing a candidate, you know what you're looking for and can explain what you need from experience.

[hawk_]

> So for instance try doing marketing yourself for a month.

People who try coding for a month and based on that try to hire a programmer make terrible clients/managers. I am not sure this advice would apply to anything that has even a little depth/nuance.

[anonzzzies]

As a relatively successful founder of multiple companies over decades, I cannot say I would like to do this. It feels like this will make you waste time on things that potentially take a very long time to learn and it might put you in a situation where a little knowledge is a dangerous thing when trying to interview/hire.

[PeterisP]

You have a point with "would be to never hire someone to do work you've not done yourself", but I can't agree with your specific suggestion on how to handle that - instead, my recommendation would be to rely on someone you trust who has done that thing, and use their help to judge expertise and validity of candidates.

It may well be that you're not qualified to hire marketers or developers, but while there's nothing wrong with getting qualified for things, that probably isn't your priority right now, so you should spend that month on doing things that matter and "simply" get someone already qualified to do that task.

And while there are many reasons why you couldn't or wouldn't hire a friend for that role, using your personal contacts to fill gaps in expertise will be very, very important; because you can't simply buy a combination of expertise and trust anywhere.

[nh2]

> I believe Joel Spolsky mentions this.

Anybody happen to know the link?

[loxs]

Do you have a good guide on how to "try doing marketing yourself for a month"? To me this shit is so alien, I can't imagine I'll even scratch the surface in a month.

[iovrthoughtthis]

1. list all the people you know in each of these sorts of roles 2. ask them to either join you or if they know anyone who might be up for it or if they would help you hire someone by being your capability sense checker 3. if you can't drag together a rag tag team then you need to go out and meet more people

previous places you've worked are great sources, as are alumni networks, friends and family.

failing that, go become a part of a community like a runner club, rock climbing gym, music scene, maker space, game jam. ideally you do these thing because you enjoy the though.

be prepared to pay people. don't hire anyone you're not confident in (if you're not sure on someone because of pay then go out and find the money [yes, i am aware this is v hard])

[NickC25]

Seconded. Get out of your office or house and become part of a larger community. Ideally, you will meet the right folks, or meet folks who know the right folks. Networking can really help. People naturally want to help others (for the most part).

Also, completely agree that you need to be prepared to pay folks, unless you are very close with them and they explicitly understand that you haven't raised, and are at an early stage. If you can't pay them, ask for simple advice and ask if you can call on them for help if/when you do raise/have money.

OP - if you don't know what you are looking for, ideally, be comfortable asking what you would think as stupid (or basic) questions. Don't worry, serious and/or good people worth working with or for won't mock you for that. Just because something is second nature to me (a product/sales/marketing person) doesn't mean it's second nature to someone who has a background in finance or systems engineering or whatever. And that's completely OK!!! People love to talk about themselves or their job or their industry, so just learn to ask good questions, no matter how complex or basic.

I myself have been in that situation recently - one of my neighbors has found tremendous success in the area of business I am currently in - so I've been able to pick his brain more than once, and because he knows I'm serious and want his help, he's more than willing to answer any question I have. Find people like this, and yes, be prepared to pay them or offer them equity if/when appropriate.

[irjustin]

There's too little context to give meaningful advice here.

What stage is your business? Pre-rev, rev, profitable? What business are you in? What part of the world are you located? Are you looking too go remote, hybrid or Co located?

Really you need an advisor if I take these questions at face value.

If you have funds to be able to hire a team (esp cyber security), then you've likely raised money or made money. If you've raised money your investors should be able to deeply help you. If you've made money, I feel like you would know what you need more than anyone here and you should just interview for your biggest problem you can't solve yourself.

[latexr]

> Really you need an advisor (…)

> (…) you should just interview (…)

But how would they go about doing that? Where does one find an advisor or the people to interview for those positions as a solo founder without experience in the matter? Feels like that is a big part of the question:

> (…) how does one start? (…) where to look for the talent?

[olegp]

My advice would be to find advisors who are experts in these skills and have them screen for them, while you do everything else. Pay them for their time in cash or options. Make sure to hire senior level people first and then have them screen for these skills in subsequent hires going forward.

Finding external recruiters that are able to screen for these skills is another option, but such recruiters are few and far between and their interests may not be aligned with yours.

At Toughbyte we do tech recruitment and have helped early stage startups hire CTOs on a few occasions where I have been the one assessing their tech skills and culture fit, but this isn't something that I have yet figured out how to delegate properly to other team members.

When it comes to assessing tech skills, this blog post I wrote is worth a read: https://www.toughbyte.com/blog/how-to-effectively-assess-cod...

Other posts tagged Hiring may also be of interest.

[seanthemon]

Yep, a strong technical recruiter can make a world of a difference

[RamblingCTO]

So now we get linkedin spam on hackernews, nice!

[onetimeuse92304]

That's a tough problem, regardless how you approach it.

The best thing is to know a lot of people and just happen to know somebody who can help you. The second best is to scour the internet and your network for people who are good at what they are doing. Trying to hire your first person on a job board is probably the worst thing you can do.

Rather than start with a position, start with the person and figure out how they can help you given their skills and personality.

This is not the time to standardise your positions, you have to make best use of the flexibility that startup setting provides and use that flexibility for your advantage.

You will have to give them a lot of freedom anyway.

Don't hire people who can't deal with ambiguity and/or need a good precise description of what they are supposed to do. Most of the work is defining what you are supposed to do so you will be getting very little value out of them if you have to provide all of the direction.

If you are starting with a vision and try to force somebody into that vision then you are already fighting an uphill battle.

[farbklang]

I started recently (2 years ago) and running a small consultancy, and using part of the revenue to build my own product.

What worked for me was starting to give out small tasks via <your favorite freelancer platform>, often giving the same tasks to multiple individuals and then decide with whom I am going to stick.

Has been pretty successful for finding talent, not sure how much my anecdote weighs in though.

Working together with friends is something I probably won't do again, it's just too easy to cross damage professional or personal part of the relationship when there are issues arising.

So if you can afford it and have the time, I would recommend starting on freelancer platforms. It also allows you to make mistakes as these relationships do not require commitment from any side. Down side of course is, that you might lose good talent as they are also not comitted to you.

[ptero]

Ideally, for first 1-3 hires you hire someone to do the job (most of which) you can do yourself. That way you buy speed, not capability.

If you really need the second person to do something critical that you cannot do yourself consider a cofounder, not an employee. My 2c.

[23B1]

Scale from 0-1 kills so many companies so I'm glad you're asking at this stage.

What you need is a 'specialized generalist' someone who knows enough to set you up for success, get the first few hires, get your sales engine going, get your ops infra nailed down.... but doesn't necessarily want to slow you down when you need to scale out the functions you mentioned.

This is how I operate basically; I help us get to 1, then I replace myself with four or five specialists that can handle those 'departments' as the company really hits its stride, and move on to the next company usually thanks to a referral from the previous guy. It's fun.

Here's what I'd consider

1. Youngish people (40s) who have done some time as a COO at a growth stage or earlier company,

2. Who've been in that role 2-3 times at various early-stage companies in your domain (SaaS operating models are wildly different than consulting services, for example). Also CFOs with diverse/soft skills are good here too.

3. Experienced folks won't work for free. They know the risks, so expect to pay; slightly under market + equity.

[em-bee]

how long are you staying with one company usually? i imagine getting from one person to five can take anywhere from a month to a year or more depending on how fast revenue or investments are coming in.

i am kind of in this situation myself. but i primarily need sales partners in regions where i want to sell my services, while the rest is done by people offshore (me included)

[Eumenes]

Ask yourself if you really need all those positions. How much dev-ops and security can you possibly need? That can be shared responsibility until you're much larger. Same with sales - you, as the founder, should be doing most of the sales early on. Its expensive to hire and to fire as well.

[saalweachter]

Figure out your criteria for failure, and what to do in response to it, in advance.

Some of the people you hire are going to be bad. Maybe they'll just be generically middling, maybe they'll be outright incompetent, maybe they'll misallocate resources and cost you thousands, maybe they'll outright steal from you. Maybe they'll just turn out to be a bad person.

Even if you don't know how to do sales, what benefit do you expect to gain from hiring someone to do it? How long will you wait to see those benefits? What will you do if those expectations aren't met? If you have to fire someone, under what conditions will you provide what sort of severance?

The most important part of any contract is how to break it.

[el_benhameen]

I haven’t done it myself so I can’t speak from experience, but Rob Walling’s book “The SaaS Playbook” has a whole chapter on hiring and building a team. I found it insightful. The whole thing is a quick read/listen and I thought it was worth my time.

[zackprice]

Regardless of how smart someone is, don't hire assholes.

A single bad apple in a new team will drag everyone down, reducing communication, causing silos (as they avoid the bad person) and just generally making work not happen the way it should.

[artur_makly]

In my 25yr experience as a serial entrepreneur, never hire full-time until they consulted with you for at least 6 months. So many factors can go wrong that are not related directly to hard-skills.

It's marriage essentially.. so date around!

[hobofan]

How do you go about finding freelancers that are willing to consider employment?

From all my experience, there are very few freelancers in general that are considering employment at all (though the percentage is slightly higher among non-devs). And for the few that are considering employment, you'd would usually have to put a lot of equity into the compensation package to make up for the (usually) significantly lower salary.

As a freelancer I've also offered that option to potential clients/employers, but clients always decline that, citing bad experiences in the past, where they've felt bait-and-switched as after the "trial period" freelancers usually want to switch over to employment.

[mateusfreira]

This is great advice ^

I run my business for over 10 years and have experimented many different alternatives, for small business with no cash to burn this is probably the best advice one could gave.

Start with consultancy/freelancing reduces a lot the risks

[pier25]

This exactly.

The smaller the business, the higher the risk of hiring the wrong people. You have less money to waste and individuals have a much higher impact in small orgs.

Minimize the risk by "flirting" before commiting to hiring.

[pettycashstash2]

You are over complicating. Start with one person and grow from there. The 1st person is the most important

[instagraham]

Bit unfair to say questions like " What questions to ask, what to look for and where to look for the talent?" are overcomplicated for hiring?

[j45]

The book buy back time by Dan Martell has been one of the more interesting and actionable books I've read in a while.

For me, generalists with experience (a lot of different specific skills) and have learned how to learn so they can solve problems is key.

A lot of thie hiring in the start, especially self-funded can be a little counter intuitive. The purpose of hiring is to free you up to work on more valuable parts of things, assuming you want to work on those things.

If you focus on hiring people better than you, it will get you more free time.

Some people rather than equity, focus on what folks are really after, payouts. Doing rev or profit share can be easier than dealing with the mess of shares, especially if you don't know if they will be devoted to it long term like you.

For sales roles especially finding someone who can become a better sales person than you, it might involve a rare exception and providing ongoing commission as long as the customer is engaged on the system, and the sales person remains there.

In terms of looking for the talent, if you are looking for fractional assistance before full time, online sites like upwork can help find the people who are ready for something stable.

The book above will give some food for thought and there are others I'm sure too.

[jokethrowaway]

I would advise you don't, until you have way more money than needed so you can buy really outstanding candidates.

Nothing can sink more your company than a bad hire because you can't afford to compete with big companies. Another option is to lose equity in the process, so you get people who actually give a damn.

Until then, outsource to agencies on the expensive side and be quick to fire them if not performing.

[austin-cheney]

If I were in your position I would start with people I know personally and I would define success criteria to hold them accountable against. I would evolve that success criteria as the mission evolves and use that as a frame of reference in hiring the next people. Prior experience in leadership and holding people accountable is required.

[rcyeh]

Echoing several of the comments here about learning by doing, I think Ben Horowitz’s “Hard thing about hard things” may recommend that too. See section (and blog post) “If you’ve never done the job, how do you hire somebody good?” with pitfalls:

https://a16z.com/hiring-executives-if-youve-never-done-the-j...

“The very best way to know what you want is to act in the role. ... In addition, ... bring in domain experts.”

[onion2k]

Ask people who have hiring experience in your network to help you by sitting in on face to face interviews. Same goes for a mentor if you have one. Try to prioritize hires who'll make that work easier.

[camila45]

Passionate explorer of products and services, on a journey to uncover hidden gems and share my experiences with the world. Dedicated to providing honest and insightful reviews to help fellow consumers make informed choices. Contatct remotespywise at gmil co m for all your hacking services. just a mail to remotespywise at gmil co m. Stay safe

[block_dagger]

Read Peopleware. It’s more about finding teams that gel than individual high performers. Makes the task even more challenging, sadly.

[epolanski]

By having a good business, giving good equity and salary and hiring top talent.

Realistically, early stage startups have a person do all of these things together and learn, they have no budget to hire talent in those roles.

If you're business is that successful without any of it..you may actually not need these people.

[bionhoward]

Check the books Traction and Who, you could make a score card for each position based on your business goals.

[ecmascript]

> Assuming that I don't know anything about or have zero experience in the skill-sets I am hiring for, how does one start?

You start by doing the tasks you need done yourself. When you learn what is needed and can't manage it yourself anymore then you know what to ask and hire for.

[nonameiguess]

I don't think there is a good answer to this, unfortunately. I can't speak as a "solopreneur" because I'm not that, but I'm a consulting engineer doing platform and infra-layer work for small businesses that don't have the resources to do it themselves, and I can at least say where and why I see them fail.

Largely, they have the problem you have. They don't know how to hire. We get some initial POC/MVP services up and running, but then it comes time to monitor, secure, upgrade, actually run the software for the long term, and they try to bring in people who can do that, but don't even know what to ask in an interview because they have no knowledge of these fields of practice themselves. The main company I'm working with right now has hired three guys to try and do all of the basic maintenance and daily operational work and they've so far fired all three. They either messed up badly from not knowing what they were doing, or at least realized they didn't know what they were doing, but also couldn't learn, and this company doesn't want to be wasting the money they're spending paying me to be a teacher, and I don't want to be a teacher.

I think my advice would be advice a lot of solos don't want to hear. Unless you're a genius polymath with at least inch-deep knowledge of virtually everything related to computing, which gets harder and harder as time passes and there is more to know, don't try to do it alone. Have co-founders that augment your gaps. Technically competent investors with expertise in how to staff at the executive level so you'll have others with you who at least know what to look in staff and how to hire, or can help you separate wheat from chaff if you're trying to use headhunters.

Also, don't be in such a hurry. Whether it's get more runway, cut costs elsewhere, I don't know, but take your time and do it right. Going through cycles of hiring the wrong person, having to fire them, and then doing it all over again, is disruptive, destructive, and will get you a bad reputation to the point no one reputable will even want to work for you.

Otherwise, your best shot is to get lucky. That happens enough at scale that the market is full of people who got lucky, but it doesn't mean the probability of success is high when explicitly using "get lucky" as a strategy. You can't just look at what the top people did and copy them any more than you can watch Usain Bolt's training videos and hope to become a great sprinter by doing whatever he does.

[giantg2]

If you really don't know anything about the skillets, maybe a consultant specialized in standing up startup teams would be a good start. After that, look for people genuinely interested in the problem domain or in their specific craft.

[aarvi]

just hire. you will figure it out. a lot of people i know often wait for the 'perfect' candidate to show up at the door in a halo of divine light. aint gonna happen. most of the 'A-players' on my team currently were hired less on technical chops and more on un-measurables like 'sincerity', 'attitude'. these same people, now, with the benefit of decades of working together, would not hire themselves as they were when they joined.

in a nutshell: for a startup as early stage as yours, you need people. you will figure out what you need as you go along.

[brudgers]

Doing those things yourself is the simplest place to start.

You need to know what you are hiring for before you have a chance of hiring the right person for the role.

At this point hiring is an XY problem.

Because your problem is sales, not hiring a sales team.

Good luck.

[vb-8448]

> Assuming that I don't know anything about or have zero experience in the skill-sets I am hiring for

My guess is that you need a co-founder that can fill the gap instead of employees.

[ant6n]

Then he won't be a solo-preneur anymore.

It seems like hiring people is much less risky than marrying them.

[zubairq]

Good write up! Agree with the top comments about hiring smartest independent people earliest

[clnq]

A thing called the Competency Framework can help.

[kidgorgeous]

Watch Alex Hormozi on youtube

[ozim]

There is advice from DHH and Jason Fried I believe.

Before you hire start doing that job yourself to understand it and hire only if you are sure you have to hire someone.

If it is only you then get at least one other smart person to share the job and go from there.

If you hire 5 people and take them “just do it” you can as well give me your money or to any other random person effect will be the same.

[broadwayinc]

If you're starting, you can hire some head hunters to do the job. Then make mistakes by hiring bad people so can you learn what to watch out for when hiring talent in each positions. You can ask what their ultimate goal is in their fields, ask them why they decided to leave their last job. Most importantly, see if they are compatible with your personality.