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.
Ask HN: As a first-time solopreneur how would you go about hiring the first team
31–40 of 103 posts
Re: Ask HN: As a first-time solopreneur how would you go about hiring the first team
#32If 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.
Re: Ask HN: As a first-time solopreneur how would you go about hiring the first team
#331. 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])
Re: Ask HN: As a first-time solopreneur how would you go about hiring the first team
#34> 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.
Then he won't be a solo-preneur anymore. It seems like hiring people is much less risky than marrying them.
There is very little context but, in my opinion, you can't be a "solo *tech* founder" without some technical skill. You can improvise a sales or marketing person for some time, but no way you could improvise a devops or security engineer. You need a "CTO" otherwise you will fail, 99.9% guaranteed.
Your cofounder doesn't need to own 50% of the shares, you can still act like a "solo-preneur" but you need people fully committed to the success of your adventure.
Re: Ask HN: As a first-time solopreneur how would you go about hiring the first team
#35In 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!
Re: Ask HN: As a first-time solopreneur how would you go about hiring the first team
#36[deleted]
Re: Ask HN: As a first-time solopreneur how would you go about hiring the first team
#37I 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.
Re: Ask HN: As a first-time solopreneur how would you go about hiring the first team
#38Scale 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.
Re: Ask HN: As a first-time solopreneur how would you go about hiring the first team
#39In 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!
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
Re: Ask HN: As a first-time solopreneur how would you go about hiring the first team
#40Doing 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.