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Ask HN: Tips for Solopreneur?
223 points by solo_prono 11 months ago | hide | past | favorite | 79 comments
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?




(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.


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.


> 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.

+1 to this.

There are definitely different models for VCs, but in general, the big "brand name" VCs are in the unicorn business. This tweet [1] does a succinct job of explaining why.

The result of this is that as a founder, if you own 49% of your company and big-VC investors own 51% of your company and someone comes along offering to buy your company for $100m, your investors are likely to turn it down. For you, that would likely be a life-changing amount of money. For a big-name VC, it doesn't move the needle. In most cases, they'd rather roll the dice and end up with $0 then get their share of a $100m exit.

[1] https://twitter.com/jasonlk/status/1670021902612549632?ref_s...


> There are definitely different models for VCs, but in general, the big "brand name" VCs are in the unicorn business.

Slightly naive question, but does this include YC? The wording on their page makes it sound like joining YC would help most startups but is that just for show? Or does this apply much more when the VC owns >50% of the company?


Take a look at the second chat at https://jaredheyman.medium.com/on-the-176-annual-return-of-a.... The vast majority of returns for YC are for the companies at the tippy top of that chart (Airbnb, Stripe, Dropbox and a few others).

YC certainly provides a nice package to founders. But they are definitely in the unicorn business.


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 `newsletter@mysite.com` setup (I got there eventually)


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


I'm glad I could help! Always happy to answer more questions, either here or via email (i'm justin@buttondown.email).


> "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)


> "what happens if you get hit by a bus?" or b) create a product for customers to whom that doesn't matter.

I simply read this as "what guarantee do I (the customer) have that you'll be around tomorrow?" I don't see where investors come in to this piece of advice.

If a big company takes a risk in locking in to your product, they want some assurances (I've seen them ask for stuff like business continuity plans, code escrow, etc.)


This is assuming someone looking for funding doesn't want to use to money to ensure the business is going to be around tomorrow and it kind of feeds into the prejudice.

I mean, what else someone would be looking to get investment for?

To get the money bags and run?


> 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?

They don't expect anything. They just want to know what will happen in that instance. Most companies derisk this by hiring other people, even though that drastically reduces profits. Telling people why they should feel patronised by reasonable questions is not going to help them navigate reality.

> 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.

This just isn't the case. No one cares about suppliers with generational wealth. If a solopreneur dies and their AWS account gets locked out and their service dies it's not about generational wealth. These memes just get in the way of thinking.


I'm not saying you're wrong (I've never tried to raise a round!) but I meant that in the context in which I've encountered it, which is in sales to enterprise/larger users who absolutely do expect that if I am hit by a bus there is someone else who can ensure continuity of service.


If someone is running the business alone, what do they look to get funding for?

To expand, grow, to hire people so that the "bus" scenario won't materialise.

So if someone asks it - they are either taking a piss or think that you want to run with their money (as many think this way of the poor).


>What do they expect to happen if solo entrepreneur get hit by a bus?

Something as simple as knowing that they can get all their data out of your system and into a similar one is already some points on the board, here. Not as reassuring as a team behind you, but it is something.

I also think (a) it's not patronising, and (b) even if it were, taking exception to that perceived patronisation would not be a useful way to increase your chances of business success.


enterprise deals will ask for biz continuity doc.


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.


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.


Yeah, it's a double-edged sword. On the one hand, you are getting a lot of money and probably a great case study for your marketing material. On the other hand, you are probably going to be asked to move your product in a direction you wouldn't have otherwise taken it. Sometimes that's great, sometimes you're just a contract software engineer for much less money than you'd get doing that explicitly. You can be wary or you can be excited, every case is different.


Rollout clauses can help with this.

For instance, don't draw up a contract blindly, mandate an install base and training as part of the package, and that contractually, it must be installed, training complete, and in process for X number of days, and in that time period requests are limited to direct support (IE, actual bugs or user questions). You should be meeting with users as much as possible during this time, if you can. Make it clear that you only want and will listen to their feedback and make changes in that respect.

Then, schedule a meeting with the users at the end of the specified period, to get a sum of all the positives and negatives of the product, and have a separate with management about whats next, what your roadmap with them looks like (if applicable) etc.

This keeps the relationship in control in a positive way, usually for everyone.

I've seen clauses like this before in enterprise contracts. If you can everyone to agree to it, they turn those fears into assets real quick, and helps manage the burdensome spam of support requests for X or Y feature.


How does “I want x feature for $y or I terminate the contract according to our terms” bring contract law into the equation. Most often you have a single person in the big org as your champion. If they leave, you leave.

There are many ways to be their bitch. Many, many ways.


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.


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.


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".


I looked around and found one or two articles that essentially said "If one customer is more than x percentage of your revenue, time to diversify. Start actively drumming up new business."

If you are so small that you can't actively look to take on more customers because they take up all your time and you don't want to gamble on hiring more help when you don't really need it, you have a problem.

This seems to be partly a self created issue. Small businesses seem to think "We're friends!"

No, you aren't and big businesses know that having dealt with enough assholes themselves already.

No one can make you work only for them but the reality is if you want to stay a one-man operation and not hire more people and this one customer is 80 percent of your revenue, the tendency is to feel like "This works!" -- until it suddenly doesn't and they have you over a barrel.


Yeah, if you've got 80% of your revenue coming from one customer, that's not great. But it all depends on how you work with your customers. In my business, things are pretty hands-off, and we have calls only a couple times a year, largely to talk about promoting our work together (our tech is a customer-facing differentiator for them, so we give joint talks at conferences and such).

I don't think there's some magic percentage, over which you need to diversify. You should always be looking to get other customers, and if you have one big one then it should be easier to get other big/medium-sized ones.


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.


Yeah, I didn't say they set out to screw them, just that it does happen.

I had a corporate job. People have trouble seeing big companies as having the same cash flow issues etc they have. They imagine they are sitting on a fortune, not that a lot of those assets are needed to just run the company.

I remember reading one story about a small company waiting to get paid by BigCo and BigCo ran into issues and then tried to stiff them on payments by saying something like "This is for the latest thing we ordered and we no longer owe you those old payments cuz (legal loophole)" and the small company updated its language to counter such claims and insist "Payment is for the oldest thing we did for you...etc"

They probably weren't trying to kill the small company. They were just trying to survive their own financial downturn.

It's why I used to think "I should collect such stories when I see them." Small businesses tend to be "The new kid" who learns this the hard way and may not survive the lesson. I would like this issue to get more publicity so small businesses get better at managing such things realistically.


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.


You can also just accept that is "best what you can earn" with the product and earn that money on BigFish and move to the next project.

It is also perfectly fine option. I just wanted to add that it never is so clear cut and one might be having "going to the moon" ideas where product is basically in BigFish niche and no other company will really use it as much and especially other BigFish2 wont hop on the bandwagon because they are competitors and will never take risk of having some part of their business in the same pot as the other.

Even if technically it is super cool or whatever.


> 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.


That's probably a big part of it.

If you undercharge on some small, one-time job, afterwards you go "Whoopsie! Time to adjust my fees. No big."

You undercharge on some big, ongoing contract and it can feel like you can't make any real changes. And now you're stuck in this bad deal. (Or at least feel stuck.)

People tend to not know how to "fire" a bad client and the idea that you can choose your clients, at least to some degree via market positioning, is alien for many people.


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!


> 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.


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.


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.


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.


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).


Solo founder works for B2C2B, and I think that's what you're looking to do based on what your examples.

Notion is actually the poster child for the strategy: you target a group of people who have the job title that'd use your product, but build something that appeals to them on personal level as consumers.

You don't bother with typical B2B messaging, no enterprise-y sales pitches, and you lean into community building.

That way your users will want to share it with their friends (who tend to be other people with similar job titles), want to bring it into their company for semi-personal-use, and eventually push for their employer to adopt it officially (and you charge them more for it as business users).

By the time you're face to face with the "Business", they've already established there's value in what you're selling and the signal is coming from the people they trust most.


For further context, this strategy is known as Product Led Growth (PLG).


Technically I'm advising them to go more towards Community Led Growth, but it's rooted in a similar place as Product Led Growth

https://www.amity.co/blog/duolingo-figma-notion-and-hubspot-...


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.


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


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.


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.


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.


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.


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.


Designers know what will help them when they see it. They don’t need sold on things that make their job easier, the way good dev tools don’t need to sell/convince developers to use them. They provide an obvious value, and people want them because of the value they can see and use firsthand. If you have to talk someone into using a dev tool or design tool over multiple emails and madmen style nights on the town, you’re trying to convince someone to see value in something with no obvious value. People don’t need marketing or convincing to buy things they see clear benefit from. Designers are a rare type who might not know what they are missing or what exactly they need, but when they see it in front of them, if it helps them, they will instantly want it and not need to be sold on it. If there is no interest from even 5 designers I’d say it’s not going to scale out to a good conversion rate. Designers are a rare type where I would argue it only takes 3-5 to say nope to know you’re not hitting any real pain point. A plugin that automates tedious photoshop workflows sells itself. Immediate value is right in a demo. Nobody has to wine and dine people on that. Just my opinion.


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.


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


Interesting


Very, interesting


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, =)


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


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.


> 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.


ok that is fair - going to SF frequently but not living there is something i should have been clearer on!

my cofounder and i go 3-4 x a year now, for 1 week at a time. it acts like an offsite - get out of usual routine, meet interesting people, do lots of meetings (we'd normally avoid this sort of thing), get ideas and up our ambition, then go home and build stuff for 3 months quietly. repeat!

in the early days, if you fundraise, then at least SF based firms are way better to deal with in general, of course with many exceptions


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.


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.


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!


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!


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.


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.


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.


About 5, to break ice with that intimidation, you can approach that world with less expectations and just approach to ask VCs and analysts "opinion". Ask them for advice and see what comes. No expectations, just casual genuine curiosity on how they would perceive your investing opportunity.

At the same time, don't feel like you have to be too agreeable either. If you have a path to profit that doesn't include investors, then that's the best thing: you incorporated potentially good advice for free, kept equity and potentially opened a door for friendship with investors that in the future might become more valuable for you.

Solopreneur are my heros, I've tried a couple of things, is hard as f*ck.


Just do it and figure out the details as you go. You rapidly learn that everyone has an opinion on what you're doing. Some opinions are worth listening to; most aren't. Arguably experience is about working out who those people are. Almost certainly nobody understands your business better than you, even now. You'll get a thick skin when you seem to fail time and again. That's normal; work out how to pick up the pieces and carry on. Keep going as long as you're having fun and are able to. The only point you need to think really carefully is when your start investing your savings.

Oh, and read The Lean Startup. And probably ignore me, my opinion is probably useless.


4) consider sharing your journey, challenges, accomplishments, product updates and demos on twitter, adding tags like #buildinpublic and #indiehacker helps. also periodically post on places like reddit in the form of 'this is who I am, this is the problem I experienced, this is the solution I have built so far, hope to hear your questions & feedback'

5) bootstrapping is super hard (doing it right now) and early on usually accompanied by some contract work on the side to sustain yourself until ramen profitability

happy to connect and point out some examples if it helps ioannis@algora.io best of luck!!


4. This post is getting some traction. Now is a perfect opportunity to tell people what it is! Maybe you'll get some interest or at least some useful feedback. Don't worry if it is still a bit rough around the edges.


@solo_prono

3. I too live in a small town in the PNW. I am looking to build a business as well in the B2B space but I think we can maybe link up and just chat about what we can do to help each other! x: @sirg_k


I'm now in year 10 of being a solopreneur. My main business is https://www.pubexchange.com, an platform that helps publishers exchange traffic with other sites, as well as buy/sell traffic. My answers below are related to that, but I've also launched https://forourschool.org, a free fundraising platform for schools, as well as a few other small sites.

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

It has never been an issue for me, but I also had that concern in the beginning. I try to be VERY responsive to emails and quickly address any issues that come up, so that usually helps address their concerns if they have any. I sometimes refer to the business as "we" (e.g. "we are rolling out new functionality"), so it may not be obvious at first that it is a one-person company, but I never deny it, and most publishers I work with and have spoken with know that it is just me.

I've worked with major publishers like Huffington Post, Aol, CNN, Time/Meredith, Yahoo, etc. Some have required approval by their information security team, which can take a very long time. There are always small issues that crop up, but being a one-person team has never stopped me from getting approved.

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?

I never really had defined milestones. I was happy to leave that behind when I left my corporate jobs. In the early years, I had so much excitement for the business and its potential that any time another publisher said that they were interested in using the platform, it gave me more motivation to spend time on it and grow it. I guess if no one said they were interested in using it, I would have questioned continuing, but it never came up.

For reference, it took about 3 months for the first publisher to dip their toe in the platform and 6 months for a full integration (god bless them for trying it!). If you are interested, the first sites to sign up were Upworthy, Refinery29, POPSUGAR, Fashionista, and Remodelista (3 of them still use it!).

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.

I'm in NYC, but I avoid in-person meetings as much as I can. They take too much time and don't provide much incremental value. I also have not had an in-person meeting since the pandemic started. So no, I don't think it matters.

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?

I have never spent any money on marketing. I send cold emails pretty often (which is mostly ineffective), but other than that, my business grows through word-of-mouth (it works like a social network, so there is a benefit to publishers to tell their friends, so that they can easily work with them). I also partner with some networks that work with many sites (such as ad yield management companies) who then sends their clients to me.

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?

I've never fundraised so can't help here. Unless you absolutely can not survive without outside fundraising, it would be stupid to even consider it as a 1-person company. Way too much of a distraction. That being said, if your plan to quickly build out your team, then sure, go for it.


Since other people are mentioning the red flags working with business critical 1-person businesses, I thought I would share a small story. When I was first starting out, I connected with Huffington Post who were very excited about using PubExchange since they were manually managing most of their traffic partnerships. For many sites, traffic partnerships can be a large source of referrals, but HuffPo took it to another level. They partnered with everybody and would link out from their homepage, so they could send a very significant amount of traffic. After a few meetings (I don't think infosec got involved), they decided to integrate PubExchange throughout all their verticals. We met in person, so they were fully aware that it was just me, but they were/are a very nimble company so they were ok moving forward. Unfortunately, because they were implementing it so quickly and using it in different ways than had been used before, the first night they implemented it, it broke, and unfortunately, it also broke all links (internal and external) across HuffPo. They took down the code, and called me that night. I fixed the issues right then (I think it took me 10 minutes) and the next day they added everything back. Never had any issues again and worked with them for many years after that.


> I avoid in-person meetings as much as I can. They take too much time and don't provide much incremental value.

Thank you for this, I've been afraid that landing clients would mean having to travel and meet people.. If I can just do video calls that would be so much better..


Where in the PNW? I'm in the Spokane area; happy to connect. Maybe I can help you out with the endeavor, or just provide encouragement. (And #3, no, it doesn't matter.)


I also live in the PNW, I'd be happy to connect to. I'm around the Portland area, willing to travel around a bit for something like this.


Check out https://indiehackers.com, a community for "solopreneurs".


I just need to get billing integration and marketing copy, analytics working for my SaaS.

I want zero coding. Just lemme pay someone to call an api when someone pays.


Congrats on jumping into this adventure! Here are my thoughts on your concerns:

1. If you communicate that you're in the early stages of building an exciting new business and wanting to get feedback from early-access customers, there should be businesses that are OK with you being solo. They will adapt to that risk, and you won't be able to sell to everyone, but it shouldn't exclude you from everyone either. You might just not be talking to the right customers yet.

2. For milestones (and fundraising) you should think about your goals - what are you trying to get out of this? Do you want to build and scale a big team, serve giant amounts of customers, etc. Or do you just want to augment or replace your income? Or something in-between? You can think about this from different angles: team size, revenue, geographic scope, your personal exit or income, etc.

Here are a couple of examples from my journey in case they're helpful:

In my prior business (https://www.bigleaf.net) my first milestone was to get a working product. I didn't feel as though just talking about it would be convincing enough (and it wasn't), but once I could demo an MVP then it really wow'd customers. Along the way I added a milestone to get a technical co-founder since I got burnt out doing it myself. Those 2 major steps took just over a year. The next milestone was getting our first revenue (took just a month or so after the MVP), then milestones just kept being added from there logically based on the strategic path we chose to be on at that moment.

In my current business (https://www.companycraft.ai) I had a mix of some early milestones. I wanted to talk to potential customers (entrepreneurs) to ensure the problems I wanted to solve matched up with pain they had, and I also wanted to build an MVP ASAP. I completed those in about 3 months, with many other smaller steps and goals along the way. My current milestone is to do a full "v1" public launch in November.

So you just set some milestones that are logical based on where you are and where you want to be in the coming months and years, then hold yourself accountable to them (or ideally be connected with a peer or mentor who can be an accountability partner of sorts).

3. On location, I go back to your team goals. If you're going to stay solo then no, location shouldn't matter. If you want to build a fully remote team then it shouldn't matter much (though being near-ish to a decent airport would be valuable for visiting the team and customers). If you want any local team members then you should think about where you'll gather and what the talent pool is like in your area.

4. It sounds like you're already on a good track here - talking to people who have the pain you're solving and gathering their emails. If that has you on the right track I'd just keep doing that. However you mentioned below that you're selling this B2B...so in that case you may want to consider if you're actually talking to the buyer of your product. Are the people you've met the people who would approve the purchase of your solution? If not, try to connect with those people. Identifying a list of them on LinkedIn and cold reaching out could be one method.

5. Fundraising goes back to your goals as an entrepreneur :) If you want to grow this to IPO or a really big exit, have a team of hundreds, and build a market-changing or world-impacting offering, then you probably need to raise outside funds at some point. However, if your desired scale is smaller and/or you see a path to profitability without fundraising then you get to keep control of your destiny, which is great. If you can afford it and you don't sense the market is going to run away without you, I'd advise continue building, talking to customers, and close your first deals; don't rush into raising money. If/when you know that you can't succeed at your goals without raising money, then dive into that path.


Hi.

1) I am same as you, I like to work alone. Working with another is irritating, to say the least. I always think I can move faster when I don't have to communicate with anybody else.

But. Doing business is less about doing stuff well and more about avoiding really stupid shit. Having other people to work with and especially a cofounder is one of the best ways to get feedback for really stupid stuff you could do.

It is all about reducing the time and cost between when you become wrong and when you stop being wrong. For some reason it is very hard to do it on your own.

2. Don't set milestones. Understand the problem you are trying to solve for your customers. Do your best solution of the problem, the best way you can. The customers are just validation of your idea -- if they come you might be onto something and if they are not coming you are doing something wrong.

3. No. It is up to you. If you are asking this question you haven't thought this solopreneurship thing yet. The whole point of doing it solo is to be able to make those decisions yourself.

4. The best way is to make a good product/service. The customers will come. Don't focus on the customers, focus on the best service you can. The more customers you have the harder it will be to focus on the service, so cherish the ability to move fast while you have no/few customers yet.

5. You want to slowly build it up. Financing is a hack that should only be used by people with experience -- not you, at least not yet.

Your goal for your first business should be to avoid getting killed financially (don't get into debt!). As long as you do that, you have ability to iterate. Most of successful people I know have started multiple businesses before they finally succeeded. That assumes ability to start another business after the first one fails. Bankruptcy will very likely put an end to your career as an enterpreneur.

Also, slowly building it up gives you time necessary to learn, to transform yourself. And build a product. It takes time to think all those things and integrate it into your experience and trying to hack it will just leave you woefully unprepared.

Also, when you get financing it suddenly puts a timer on your business. It puts a pressure that makes it difficult to focus and make your own decisions. Everything from now on is a compromise. And, at least in my mind, this conflicts with trying to build the best product you can.

Also, when you get financing, the cost of that financing will depend on how risky the investment is (I am kind of expert when it comes to risk). You don't give loans for nothing, you want to earn some money. And the riskier the investment, the more you want to earn. And as a first business with an unexperienced founder, running solo, you are as risky as it can be. If you ever get somebody to invest money in your business it will necessarily come at an exorbitant price and you are also very possibly get abused by somebody with much more experience than you.




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