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

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

#91

Earlier quoted context omitted.

"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…

I think this is the top hiring mistake for startupS - hiring the big cheese from BigCo who turns out to be a total culture clash. I do however disagree with your final paragraph. We had a few wantrapreneurs who were usually moonlighting and clearly didn’t want to be there.

"few wantrapreneurs who were usually moonlighting"

Yes that's the potential downside. That's why I said "almost" who cant do their own thing. That difference is very slim.

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

#92
post #81

Earlier quoted context omitted.

True. But it’s not only about thinking. In my experience it’s also a lot about the need for validation/ general independence. Many people (or even most?) need attention and regular pats on the back. Providing 10 people with this validation and attention can be a full time job.

This is about learning management and reminding them that the problems they might come to you with are the ones you hired them to solve, but you can drop what you're doing to help them if they need.

Not so much. I’ve been a manager for over 10 years and I can tell you people vary greatly in how much validation and attention they need from their manager. If you hire the right 10 people you can have uninterrupted stretches of time to do deep work yourself. If you hire the “wrong” 10 people then you can’t (were wrong is in quotation marks because they may not be the wrong hires under other circumstances).

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

#93
post #15
post #12

Earlier quoted context omitted.

But doesn't doing X for 1 month make you a charlatan? For example, consider you only did frontend/ui/ux for one month. How much rubbish you would pick up over that time by googling for tutorials or watching youtube videos to get you started; and how alien a real front-end veteran would look to you.

You’re a charlatan if you I think that after a month you’re an expert. As long as you’re honest with yourself it can’t hurt to have some direct experience for the role you’re hiring for. A lot of people applying for the job won’t even have that month.

Agree - I think the whole point of the exercise is so one learns the most basic macro understanding of what the business needs from that point (marketing, sales, product, finance, etc) so when it comes to hiring the right people, you at least know the right initial questions to ask.

When I started my business (non-tech), i knew very little about sales processes or relationship building from a sales perspective. One of my first consistent customers (disclosure: he is also a close friend) is a sales professional. I learned the very basics of sales, and came to him, asking what were probably dumb or basic questions, but he was more than happy to answer them and also point out where, as the company grew (and hopefully grows!), what to look for in sales people and relationship managers. While I still know little in comparison to him, I know some of the right questions to ask, what to expect from those questions, and what sorts of answers I should be looking for. He also knows that I can call him with deeper questions and to help me evaluate a sales-related situation as it arises, and he'll give me a no bullshit honest answer.

Find people like that.

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

#95
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.

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

#96

Earlier quoted context omitted.

Yeah, the whole quote is one of those things that sounds like sage wisdom until you consider it for 30 seconds. Even if startup founders had time to spare spending a month learning how to doing each and every task they needed to hire for (and trading money they have for time they don't is the whole point of hiring) they'd (i) have no time left to focus on the core business (ii) do a really bad job and (iii) having ba…

It’s all so situational. In an early stage startup you really have to focus on the most critical things. I would question doing a lot of marketing early when it may be more important to do sales or just low scale, high touch customer testing/research. If it’s not worth your time to do it personally there is a huge risk in trying to hire someone to do it. The reason is that most people with the credentials to “run a f…

I agree it's situational (there's also a good argument that e.g. being a pretty mediocre customer-facing guy is an extremely useful learning curve about customer needs for a very early stage technical CEO despite what they don't learn about enterprise sales). The general nature of the advice was part of the objection to the original comment.

If you're really motivated to participate in x you should try, if you're a bootstrapping solopreneur you may have no choice, but if you're looking at mitigating hiring risk, a month trying to code/sell/design outside your comfort zone doesn't really move the needle on figuring out how to evaluate programmers or whether your startup actually needs a sales team. (If anything, you're more likely to get the wrong answers from the DIY approach because maybe the sales function actually would be beneficial if it was carried out by someone who could sell...).

That's where you get more insight in less time from leaning on people in your network who actually are marketers or salespeople or product people to get a view, especially if they're not financially incentivised to propose a particular route.

If you want to mitigate the risk that ICs need structure and resources, you focus your hiring on candidates that have worked without structure and resources. But even having a codebase written by someone learning not to rely on Scrum meetings and JIRA tickets to prioritise is still better than having one written by someone learning to code.

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

#97

Earlier quoted context omitted.

It’s all so situational. In an early stage startup you really have to focus on the most critical things. I would question doing a lot of marketing early when it may be more important to do sales or just low scale, high touch customer testing/research. If it’s not worth your time to do it personally there is a huge risk in trying to hire someone to do it. The reason is that most people with the credentials to “run a f…

I agree it's situational (there's also a good argument that e.g. being a pretty mediocre customer-facing guy is an extremely useful learning curve about customer needs for a very early stage technical CEO despite what they don't learn about enterprise sales). The general nature of the advice was part of the objection to the original comment. If you're really motivated to participate in x you should try, if you're a b…

100% agree to all of this. There's an interesting balance of domain knowledge/skills/experience and potential/learning speed/adaptability. You are ostensibly hiring for the former, but the latter is a multiplier in a startup environment. A huge number of candidates will be in the 0-1 range compared to a more structured company. You need the >1 folks.

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

#98
post #75
post #38

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,…

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)

You're basically correct, it can be anywhere from about 6 to 18 months. Lots of variables determine that; if they're more experienced it can be as simple as getting them to a certain revenue number sufficient to replace me, or as complex as "we need to get the board comfortable with how we operate" which can take longer.

My stated goal from day 0 is "I'm here to replace myself" which applies a lot of the (good kind of) pressure to install systems or processes that are well-defined, repeatable, scalable, and then hand the whole package off to the new folks.

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

#99

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…

> I believe Joel Spolsky mentions this.

Anybody happen to know the link?

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

#100
post #62

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 qu…

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.

Your description reminded me of Karl, Homer Simpson’s assistant for one episode
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