Ask HN: Tips for Solopreneur?

[solo_prono]

Yo HN! I have been working on some design tools in my spare time to solve problems I've faced over and over, and I'm thinking about monetizing them.

I've been to some conferences recently and talked to a lot of people who have these problems as well, and they're keen to try it out. I have collected some emails, been communicating with them a bit and even got beers with one of them recently!

Here's my list of concerns:

1. It is just me - is that a red flag? Some people have asked me about my team and I told them it was just me. I got the feeling that it may have turned them off because the conversation kind of ended right there. To be fair, after that I did say that it is just me right now BUTTTTTTTT why that is okay due to my experience and work history. However, yes it is my first time doing a business.

2. How do I set appropriate milestones for me to reach? Do I think about reaching 100 customers before reaching 5 recurring customers for example?

3. I'm in a small town in PNW. Does that matter if this will be an online thing anyway? Why or when do people move to big cities like Seattle/SF/NYC/Austin etc.

4. What are some ways to do marketing? Should I even think about that before I have a few customers who are using my product consistently?

5. I've been inspired by the Startup School videos. Honestly though I'm not sure about fundraising and all these things, it seems very intimidating to me. What's the difference between those things and starting a company and slowly building it up?

[jmduke]

(Context — I run Buttondown (http://buttondown.email/) as a solo founder, with a handful of contractors on support/documentation but no other W2s.)

1. You need to either a) have an answer for "what happens if you get hit by a bus?" or b) create a product for customers to whom that doesn't matter. In general, people really _like_ being able to chat with the founder directly (lean into that! it's a superpower!) but feel very anxious about committing $X0,000/yr to you.

2. It will be somewhere between "vanishingly rare" to "non-existent" to feel like you are moving as fast as you should be. Instead of setting milestones and thinking about metrics, _especially_ in the early goings I'd focus on just spending as much time as you can on critical-path work (chatting with customers, chatting with prospects, improving core flows.)

3. This does not matter. I moved from Seattle to Richmond, VA last year and literally nothing changed about my business.

4. This is a very broad topic that is hard to answer concisely, but the closest answer I can give is "figure out how your first five users found your product and then figure out how to find more people like them".

5. Venture capital is a tool by which you exchange agency for large sums of money. There are a lot of great businesses that require more time, energy, and money than can be provided by a single engineer working for an indefinite amount of time; there are a lot of great businesses that can be built without those things. I would not take a lot of stock in any prescriptive answer that says you HAVE to take VC or you HAVE to bootstrap; it depends on the type of company you want to build and what you consider a successful way to spend a decade or so of your life.

[ye-olde-sysrq]

VC can be a great way to break into markets that just have inherently large moats or barriers to entry. Stripe is an example: you can code all you like but you literally can't move money without going through a ton of very annoying (to devs, anyway) footwork to get cozy with the existing financial institutions. The connections your VCs give you can matter as much as the money.

They can also literally kill your company. VCs have a very specific strategy: they give some money to 1000 companies knowing that 990 of them will return 0% in the hopes that of the remaining ten, 9 of them return %X000 and one returns %X0000. Given this, they are going to have very little interest in finding a company that will return even "good" results. They're going to push you to shoot for huge growth or die trying. And given the choice between "grow modestly and safely" and "grow faster but risk exploding" they will push you to pick the latter, because in their business model they can't even count low enough to measure returns that are just 10x.

[Mockapapella]

Oh hey, I use buttondown. Love the service, no fluff. The only point of feedback I have is that the terminology around hosting from a domain vs sending from a domain was kind of confusing. Wasn't super clear how to set things up for a simple `[email protected]` setup (I got there eventually)

[jw1224]

This was a helpful and really informative comment. Thank you!

[varispeed]

> "what happens if you get hit by a bus?"

This is actually a weasel sentence for "you are too poor" and it's kind of patronising. What do they expect to happen if solo entrepreneur get hit by a bus? That he or she has like a dead man switch that will send over all the business secrets, IP, passwords etc to a trusted person to ensure continuity?

In reality the rich look for business run by someone with generational wealth or someone who already made it and they don't trust the poor. There is an exception if they want to make a token investment, like helping the poor or disadvantaged will get them a badge in their social circle or they need it for PR.

People run their business on their own mostly because they don't have money to hire a team that will "survive" owner being hit by a bus.

So if a potential investor asks that question, it's better to politely turn them down. They are not genuine.

(I attended many seminars for angel investors, VC funds etc. and that's my take away)

[DoreenMichele]

Something that seems to be not well known by the general public:

Landing a big contract with a big company early on can be very problematic. They have a history of screwing small companies.

Small companies often seem to imagine this will solve all their problems. It seems to be the business equivalent of the fantasy of winning the lottery and then having it made in the shade. In reality, winning the lottery frequently doesn't end well and landing a big contract early on often doesn't either.

I used to imagine I would keep a file of such stories but never did. It's been challenging to find examples when I want them. But it also seems to be common knowledge in some circles.

Feel free to bite off more than you can chew and view it as a growth opportunity, but be aware that getting too much of your revenue from one client makes you their bitch. It's like all the downside of being an employee plus all the downside of running a business.

Best of luck.

[GabeIsko]

Landing big contracts as a small company - it's not all bad. They can bring in a lot of revenue, for not that much sales effort. And if you have good processes down, they can also be much easier to deliver on. At least in the US, contract law can be very fair, financing options to facilitate large contracts are plentiful, and most large businesses act in good faith.

So it isn't so much landing a big contract is bad, but landing a big contract that you can't deliver on is very bad. Determining what you can and can't do, how much you need to invest into your internal processes and capabilities - that is the challenge of running a business.

Usually, in successful businesses I have worked at (or business units), I see a split. Ideally it would be 50-50 large contracts to small accounts, but usually realistically is is more like 60-40. Probably depends on the industry too.

[Klonoar]

I ran into this early on and it’s a very tight rope to walk. You’re early and trying to keep the big fish so you over-extend and then you’re stuck with that level until you figure out how to reset the expectations - which can be tricky to do.

It blocks you from doing other more critical things that, while they might not make you revenue today, will potentially make you revenue later.

I’ve never been a fan of VC money but if you’ve gone through this kind of bootstrapping you can certainly appreciate some of what it solves - tho the grass is always greener and all that.

[dmuso]

Yeah this happened to me and it killed my business. I didn’t have enough time to expand the business and I didn’t charge the first customer enough to scale it up with employees.

It was really the stress that killed it. Being in that situation was not fun and I ended up burning out and telling my big customer to go jump. They threatened to sue me and I was done so I just said “give it your best shot”. Nothing came of the threat in the end. The experience has left a lot of scars and after 15 years not all of them have healed.

[gnicholas]

I can see how this might happen, but it's also a very good way to establish credibility with other customers (and funders, if you're looking to go that route). IME, it all but eliminates questions about "are you too small?" if you're already doing business with a big, well-known company.

You should try to ascertain whether they are likely to be aligned with your other customers in terms of feature development, and seek to find other large-ish customers so that you're not totally dependent upon that one. You should also try to make the dependence bilateral — make it so that you're delivering tons of unique value to them, so that they can't say "add X feature or we're dropping you".

[hermitcrab]

In my experience it's not so much that they are out to screw you. It is just there is a mismatch when a big company buys from a small company. Big Co has long sales cycles, needs a lot of paperwork done, wants training, may need consultants onsite etc. Small companies are not generally well set up for this. Also your income is more predictable if you average 1000 customers paying $100 per year, than if you average 10 customers paying $10,000 per year. Also a few big paying customers can push you around in a way that lots of smaller customers can't.

[Cpoll]

I've seen this firsthand. If the relationship isn't well managed, all resources go to niche big-customer use-cases, and the product stagnates.

[varispeed]

> Feel free to bite off more than you can chew and view it as a growth opportunity, but be aware that getting too much of your revenue from one client makes you their bitch. It's like all the downside of being an employee plus all the downside of running a business.

One mistake is charging the client with thinking that you will be able to service the contract yourself, but fee being not enough to hire a capable employee and have nice profit on top of that.

Rule of thumb - if the client doesn't want to pay you enough so that you can hire someone or even a small team, with everything that goes along - office space etc and you can't have a profit on top, then this is not really a client, but employer who wants an employee without having to be actually responsible for one. It's not a business relationship.

[jacquesm]

Just you is also a plus: nobody to convince, 100% focus on the product. If you can hack it for a while like that until you need to bring in more people it may work to your advantage, unless you don't like working alone. One thing it will save you from is co-founder trouble (which is pretty common). One thing where you'll be week is criticism of your ideas and implementation, try to find people to have these roles for you in your network, this can be completely remote.

Save. Whenever you can. Make sure you have plenty of money in the bank once you have some surplus, one day you'll need it and the size of your bankroll will determine whether or not your first crisis will be your last.

Other than that: where you are can be an advantage if the cost of living isn't high.

Marketing: make sure your customers are happy first, then ask if they can be used as references, plenty of them will go to bat for you if your product is good. They might even give you referrals. Good and happy customers >> marketing budget.

As for fundraising: unless you have a very solid plan I wouldn't bother for now, first get your stuff established a bit and then when you have more substance if you are still interested in raising funds you could do it but make sure it is an option and not a must because otherwise you will hand control to your investors before they're even on board (and they are pretty good at detecting that).

best of luck!

[jedberg]

> It is just me - is that a red flag? Some people have asked me about my team and I told them it was just me. I got the feeling that it may have turned them off because the conversation kind of ended right there.

Solo people and even small teams are a huge risk to enterprises. They will have to dedicate time to negotiating with you and integrating your solution. If you just disappear after that, that's a huge problem for them.

Fog Creek talked about this a long time ago, where they priced their B2B product just below the typical limit for an engineer to expense, so that engineers could just buy their product online with a credit card and expense it. Once you enter into vendor vetting, it will be really hard to get out of it.

[SoftTalker]

Be aware that more and more large orgs will have policy around software and services procurement for any software that will run on or touch internal enterprise systems or data, particularly protected data, regardless of price. This isn't 2004 anymore and engineers or even managers cannot just expense software purchases. It's only gotten harder to deal with big enterprise as a small software or services supplier.

[philsnow]

There's a pricing death valley in between "can be trivially expensed" and "needs to Go Through Purchasing"; there is a huge step function in the cost for you, the vendor, to sell into that enterprise that occurs right at that cutoff.

"What costs? I sell bits over the internet, my marginal costs are zero!" I mean the cost of either your time managing an enterprise sales cycle yourself or hiring somebody to do it so you can actually work on your product, times many many potential clients (because most will fall out of the sales funnel, so you need to have lots in flight to get some in the door by the end of the month).

It can be untenable to price a product anywhere between $500/mo (or whatever the cutoff is) and $20k/y.

[gnicholas]

Regarding (1), are you selling B2B or B2C. I've found that B2C customers typically don't care that much, and if anything they are happy to be communicating with the founder. This is true once you have something built. It may be different when you're still at the idea phase, and thinking about building.

B2B customers will definitely care. Some will ask you to have millions in insurance and source code in escrow before they'll work with you. But there are some out there that are more flexible, or who just don't think about it that much.

Regarding (3), it's good to be in a big city for networking purposes, but these days it doesn't really matter that I'm in SV. I go to meetups only occasionally, and most of my networking happens at conferences. If you're finding it's hard to talk with customers remotely, then I guess it would be worth it to consider relocating. But I'd prioritize keeping the burn rate low, which means your small town is going to win out over a big city.

[solo_prono]

Thanks! I am selling B2B. However I guess it is more like Figma or Notion or some of these apps, where anyone can use it (individuals or companies).

[takinola]

1) As mentioned by another comment, B2B customers may care about the size of your team if you are doing something business critical. From their perspective, they don't want to depend on a product that may not be there if one guy gets sick, takes a vacation, flakes, etc. One approach I have seen some people take is to answer something like "the team is under 10 people" which is technically true (ish)

2) A startup is about risk management. At the beginning, there are ALL the risks (can you build it, are you building something people want, can you find those people in a scalable and economically efficient way, will those people pay enough for the product, etc?). Your goal as a founder is to quantify and reduce those risks in a methodical way. Your milestones should be tied to that goal. For instance, to address the first risk listed, you can set a milestone for developing a prototype. For the second, you can set a milestone for getting the first live customer, and so on and so on. My suggestion is to prioritize risk and set your milestones to address the biggest first (hint: it almost always is figuring out whether anyone even wants what you are building). Another thing to consider is the psychology of progress. Momentum feeds on itself so it is a good idea to set aggressive timelines.

3) Theoretically, no one cares where you live. Practically, it may help to be in a tech-dense area for networking, hiring, etc purposes.

4) Not doing enough (any?) marketing is probably going to be why most technical founders fail. The problem for the most part if not whether or not you can build a thing, it is going to be whether or not you can get enough (any) people to buy and use the thing. You should be doing twice as much marketing as coding as a rule of thumb.

5) Fundraising is a tactic, just like any other tactic available in building a company. There are some ideas that are capital intensive (eg high customer acquisition costs) and would be hard to execute without fundraising. If you do decide you need/want to fundraise, you should understand the implications for you and your company and plan accordingly. For some reason, lots of people seem to form their identity around bootstrapping or VC. I don't think this is a useful way of thinking about the topic. It is better to think about it as a tool and decide if that tool is what you want or not.

[sjducb]

#4 is so critical. How do you plan to get users without marketing?

[yread]

Regarding 1) you can try to appear bigger than life sized:

Get an advisor or contractors or business developer and put them on the "team" page

Make PR like announcements on LinkedIn or Twitter or your newsletter - try to copy the style of corporates

Do free trials/collaborations with midsized customers and then list them as customers on your landing page

Get references from your end users. It doesn't even have to be key opinion leaders but if they are in the business try to get them to agree to a statement and that their face and title would be on your page.

Get a part-time employee if it's possible for your customers to find out how many employees you have.

[sjducb]

Appearing bigger is super important. I remember a startup where we rented offices on 3 floors. Top floor was one tiny room with the MD in it, bottom had the business development guys and the middle had 12 engineers. Regularly they would bring prospects in and say “this is one of the offices, there’s another one above and below. Then they’d usher the prospects to the big shared meeting room.

They got loads of deals done and the company grew big enough to need its own building.

[dgudkov]

1. It's definitely not a red flag. Solopreneurs can be successful and grow businesses to non-trivial levels of revenue and income. I myself went that path, there is absolutely nothing wrong with it. I'd even argue, being solo should be the default option rather than an alternative.

2. There are 3 phases for your business:

   - Verifying product-market fit (this includes getting at least 1 paying customer)
   - Finding a way to get a more or less stable stream of new customers
   - Building up an organization

3. Running online business from a small town is a dream many chase :) At some point you will need lawyers and accountants, you will have to figure out how to deal with them remotely (that shouldn't be hard).

4. Marketing will become one of the hardest parts of your business once you verify product-market fit. Have at least a newsletter and a referral program - they cost little but work.

[wutwutwat]

Design tools shouldn’t be hard to sell if they are useful to others. The product should very much do the sales for you. These people know of your product, you’re exchanging emails and getting beers, and yet those people aren’t coming to you and asking how can they get access. Design tools specifically don’t require rubbing elbows with folks over beers to sell, not if it’s useful. Designers will have zero hesitation jumping on something that saves them time or makes their workflows less tedious.

No offense intended but if other people found value in it you’d be making sales and they’d be praising it to their designer friends. Design products that people want are easy sells. This is a smell you don’t have product market fit. But, that’s ok, because it’s a thing you built for you, so if it doesn’t solve anyone else’s problem you’ve still solved your own. If your product has competition, how are they able to sell to folks? Are they small? Maybe it’s niche and there’s just no market to penetrate.

Why the b2b targeting? Aim it at b2c and skip the enterprise bs. Again, if it is valuable to designers, they will purchase for themselves personally and use it at both work and at home, and that is frictionless compared to contract negation and vetting, snail paced security audits, and nonsense terms and scope creep added to sign a deal. It’s not needed here imo and it’ll force you to sell your souls to get deals and your passion project will morph into a monster you don’t even like.

[vsareto]

You probably still need a decent sample size when finding a market fit, so I wouldn’t write it off as not being useful unless there’s been 10-20 impressions.

[quadcore]

Some people have asked me about my team and I told them it was just me. I got the feeling that it may have turned them off

Repeat after me: emotional intelligence and situational awareness. You've been asked that question not for the answer but to see how you'd respond to it. He knows you're alone. So he asks. Will you loose your shit? Will you understand what he's trully doing? Have you prepared for it? How come you let such an obvious hole in your defense?

Dont ever ever make the mistake to think people are dumb. They play dumb. Most people are engineers just like you. Except they dont do the same engineering than you do. They do emotional engineering. People love it. They crave for it.

Do you get it? If you're not sure, then you dont get it. So get it. People dont trust an emotionally dumb person. Period. Trust me I know.

Thats your answers to all your questions but the product. You will sell once you're emotionally smart because of the strong effect it has on people.

[soneca]

What? This comment feels like an intro to sell a “be emotionally smart” on-line course.

[Joel_Mckay]

1. It is just me - is that a red flag?

You are not big enough to drive enough revenue to grow yet. A company takes a lot of work besides a few good ideas, and most people just can’t afford to risk sweat equity. Asking software/engineering people to work for “free”/”shares of nothing” sours most conversations pretty quickly. People with skills usually get scammed once or twice before they learn this lesson.

2. How do I set appropriate milestones for me to reach?

You are currently in the independent-contractor or owner-operator class. If you plan to self bootstrap, than don’t enter into a public market without a war chest over $500k. You will need to hit hard and fast in a very lucrative/narrow niche, then bail-out of the sector before an army of losers show up to compete. A small team of 5 can do a lot, but focus on hard small problems if you want to survive. Recall people don’t make money writing software, but rather reselling the same product/services many times over.

3. I'm in a small town in PNW.

No, your product in hand at a trade-show is all that matters, and a small office for meetings is like $600/month. Again, think about disposable-products and services as you can’t protect anything yet. Strategic truth means not volunteering information that can harm your position. The only difference between a bum in a cheap suit and a CEO is money.

4. What are some ways to do marketing?

Trade-shows and related events where in-person meetings are more probable, and listen to what customers are shopping for at first. Each event is usually worth about 5 months of online marketing in terms of sales leads.

5. I've been inspired by the Startup School videos.

Most startup rants are BS stories of winning a lottery… No one relevant shows up to an event with 450 competitors and talks about what they are planning.

YMMV, =)

[sebastianconcpt]

Have you read this one? http://www.paulgraham.com/ramenprofitable.html

[james_impliu]

1. Just be yourself, proudly. Some people _will_ hate it, others will love it. Getting product market fit is so damned hard, you are way better off looking for a smaller number of people that love you.

2. I'd shoot for 5 reference customers (paying list price, using it as you'd expect and genuinely delighted). Along the way I'd track who you try to sell to in a spreadsheet (including those that just drag on and never close) and I'd score them across the behaviors/things you would expect your target audience would have in common. This will help you create an Ideal Customer Profile - which you can then target more and more heavily (where you do marketing / what you build next and so on in future). Be _very_ specific not just ie by industry. For example, paypal targeted ebay power sellers in the early days.

3. Absolutely not. I've more than 40K customers at my startup and I live in a village no one has heard of in the UK.

4. Don't worry about scaling up via marketing until you have 5 reference customers (and generally do more of what got you the first 5 as your first step)

5. Read Secrets of Sandhill Road to understand the VC model more deeply. If you bootstrap - you have total control, might make more if you sell (because of how preferred shares work) but it will probably cause you more personal financial stress. Decide what motivates you - lifestyle business or trying to build a $10bn company. VC is an irreversible door, more or less, whereas bootstrapping isn't. I'd default with bootstrapping if unsure.

[avarun]

> Absolutely not. I've more than 40K customers at my startup and I live in a village no one has heard of in the UK.

Haha this made me check your profile — don't know if it's quite fair to say PostHog is proof that you don't need to be in SV to succeed given that you guys went through YC and also started in a remote-first (mid-pandemic) world.

[chrisaycock]

Put a product into users’ hands.

Before you worry about recurring customers, fundraising, co-founders, or anything else, just get a minimum-viable product out for people to play around with.

The other stuff will come later; for now, you need feedback on what you’re doing. And that feedback is only valuable if the person giving it to you has experience with your product.

[sjducb]

I used to think this till I tried it. I built a product and users weren’t willing to even try it.

Now I try to validate that users want it before I build it, easier said than done.

[hermitcrab]

1. There are plenty of 1 person businesses. I have run basically a 1 person software product business for 18 years (with a bit of help from my wife with admin). I never lie about it being just me, but I don't shout about it either. A lot of my customers seem to assume that I am a team of people in an office in the US.

2. Just concentrate on getting those first few sales. It may never happen.

3. It depends. If you want to raise funds and recruit lots of people, you should probably be in a big city. If it is just you, you can be anywhere.

4. Big topic. It isn't enough to do stuff, you need to also tell people about it (marketing). The best marketing channels vary a lot depending on your product, goals, personality, budget etc.

5. Big topic. I prefer not to deal with investors and bootstrapped my business with my own savings. Venture capital allows you to launch bigger and faster, but with a lot of strings attached. I suggest bootstrapping, at least to start with, You can always try to raise money later, if you have some customers.

I have written various stuff about marketing and running a small software business over the years. You might find some of this useful: https://successfulsoftware.net/starting-a-microisv/

Good luck!

[danhodgins]

You either need to:

1. Spend time getting good at marketing (read books, do the work, get feedback). 2. Spend money for an agency or consultant to do it. 3. Spend equity and/or profit sharing for a partner to do it.

No marketing is not an option.

At its simplest, marketing is nothing more than:

1. Repeat exposure to branding and messaging over time to build familiarity

2. Direct response (in-person or online messaging designed to produce some type of response, right now)

3. Positioning: your 'lane', the unique space you ocupy in the market, relative to competitors.

Clarify your value proposition(s) first, and then you'll need to determine how to make a simple presentation about your product.

I use the word 'presentation' more broadly to encompass any type of communication piece about your product.

Tip - study advertorials. They force you to create editorial content that relates to your product that is more story or customer-driven, and is often far more effective than regular ads highlighting features or benefits.

You can then drive paid media PPC/CPM traffic to your advertorials, and then hit them up with direct response retargeting / remarketing ads after pixelling them.

Be prepared that no one will respond during the first interaction or touchpoint. It requires many touchpoints to develop trust and familiarity.

If you're going to spend on ads, try to 'capture' them somehow - into a FB group, email list, etc where you can get in front of them for free the next time.

So, make friends with the concept of repeat exposure and advertorials, and get busy. Good luck!

[richardw]

Spend some time around Rob’s universe:

https://robwalling.com/

There are a lot of people like you. You don’t need to move and you don’t need to hire anyone unless you want to. You need product market fit and the ability to learn. Find others to speak to, maybe go to microconf.

[philsnow]

Agreed; every site has a bias, and HN's is probably more moon-shooting than others. If you're not attempting to become a billionaire, it would be worth your time to ask these questions around other places where solopreneurs hang out like indiehackers.com.

I came here to recommend particularly Rob (and host emeritus, Mike)'s podcast, https://startupsfortherestofus.com/ . It's tactical instead of strategic, so sometimes that means the older episodes don't apply as well anymore, but they have a "greatest hits" list of episodes with content that's more evergreen.

[el_benhameen]

I’ll second this advice, and add that he recently released a new book, “The SaaS Playbook”. It has a lot of concrete advice for the kinds of issues OP is asking about. Never met Rob and not getting anything out of the recommendation; I just really enjoyed the book.