How should I start?

Hey all,

I’m Fred, and I’m a wannabe entrepreneur, and I would love your advice.

Last year was a great year. After spending a few years working on ambitious side projects but never launching, we (Mike & I) launched seven projects, each with their own learnings. Simply put, we learnt a lot.

That said though, in the grand scheme of things, we’ve learnt nothing. We invested a year into greasing our launch wheels, building our launch muscles, whatever metaphor works for you. That was our aim, it was important for us, and we did it.

Now though, our aim is to launch a successful business. We want to bootstrap it on the side. Our aim is to quit our jobs as soon as possible, with the (seemingly) very ambitious goal of 1st Sept 2017. Just over 18 months away. Realistically, based upon napkin math, we’ll need around $120k ARR to pull that off, as Mike has a house and I will hopefully have one soon.

So here’s where we’re at, looking to start a business, and not really having a clue. Sure, we know some stuff, we’ve read The Lean Startup, The Hard Thing About Hard Things, etc. But we’ve never done it, never actually tried.

You have though, and I’d love to hear your advice.

What should we look to do? How do we choose an idea? Do we look for a clear route to monetisation, or look to make something awesome more than a simple money spinner?

As I say, our goal is our ‘freedom number’, but we don’t know the best route. Any advice massively appreciated. If you need more details just ask and I’ll say.

Thanks all.

What should we look to do?

Well, what are you good at? What interests do you have that you are or could become an expert in? While it’s nice to have a goal to make money, you’re going to be way more successful if you’re enjoying the product/service you’re in business with.

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I suggest you think of 3 possible businesses you could start and for each describe:

-what problem you are solving?
-who is the customer?
-how you will promote it?
-what you think they will pay?
-who is the competition?
-what is the smallest v1.0 you could do that someone might pay for?
-how are you different - why they might use you rather than a competitor?
-how long it is going to take to release v1.0?

Then let the good people here tell you which ideas they think might be most viable.

Most of the people here are too busy with their own stuff to steal your idea. And if your idea can be duplicated after reading a brief description, you’ve got bigger problems.


Hey Shane thanks for the response.

We’re good at design, front end & back end, so got the whole design & dev down. What else are we good at? Launching side projects, I guess. Other than that, we both like quite a lot of standard stuff, like music, football, reading, learning, etc.

I totally agree with the general advice of doing what you know, I just worry that a lot of what we know is what most other makers know, which means anything we create in that area would be highly competitive.

Appreciate any thoughts you have :slightly_smiling:

Hey Andy, appreciate the response! I’ll have a think about our top 3 and post them up soon. Totally agree on stealing the idea, happy to share them just need to finalise the best few to share :+1:

I’d suggest trying to look for problems instead of ideas, if that makes sense?

Maybe go to some meetups or otherwise try to meet people/companies in areas you would like to build something for (possibly businesses/departments you know have money to spend?). Ask around what problems people have. Maybe even offer your time free of charge to build some small piece of software to help with their business. What would they ask you to do if you gave them a week of your time? Rinse and repeat until you have something which looks like a problem a bunch of people identify with, and are willing to pay to have solved.

I did something similar although mostly by accident :slightly_smiling:


Thanks for the thoughts Robin :slightly_smiling:

I totally agree the focus needs to be problem based. We’ve got some thoughts in that direction, but not yet found something that ticks the boxes we’re looking for (a real pain point, reachable market, monetisable as a side project to earn a healthy amount each month).

Agree on getting involved in the target community, and intrigued by the idea of making stuff for them for free. I think we’ll look at building something in the rough direction/market we want to go in and hopefully learn as we go about what people want in that area, or possibly find other applications/markets for what we build.

Ok so finally responding to this, have been having a think over the past ten days or so.

Possible Business #1: FlashTabs
What problem you are solving?
People want to learn, but people are busy. FlashTabs is an existing Chrome extension that gives you Flashcards in your Chrome new tab screen. It’s actively used by 4,000 weekly users and has had little love given. We’ve got a tonne of feedback in and have lots of ideas as to how we can improve it.

Who is the customer?
Individuals looking to learn new skills.

How you will promote it?
On the Chrome Extensions store, already included in some collections on there, and if we built a marketplace around this I think we could crank that up.

What you think they will pay?
There’s a few routes we can take.
1: Charge for prepackaged decks. This would be micro transactions.
2: Put adverts in. We currently have about 190,000 monthly pageviews in the extension and could push this number up with development.
3: Don’t monetise at all yet, build a great free marketplace of decks, and look at monetising later, or doing a spin off product, so FlashTabs is the umbrella, then we’d have a free Chrome extension, and something else that people might be more inclined to pay for. Unknown.

Who is the competition?
Anki, and others out there, but haven’t seen anyone else bringing learning into the daily flow like this yet.

What is the smallest v1.0 you could do that someone might pay for?
Probably would require building out a marketplace, and getting curated decks up. Either that or putting ads on and making some premium features, so people can upgrade to remove ads and get access to the extra features.

How are you different - why they might use you rather than a competitor?
You don’t have to go spend time to process through your flashcards, it becomes part of your browsing routine.

How long it is going to take to release v1.0?
Could probably do the ads and premium features in a 4-6 weeks.

Possible Business #2: Digital document solution
What problem you are solving?
There are too many physical documents coming in, this would allow you to tag your documents, and file them away. Then you can find them easily be searching ‘all letters from my bank’ or ‘all invoices between April 2013 & April 2014’. There would be lots of problems to solve around this space too, as physical documents has lacked innovation, but these would require scale.

Who is the customer?
Millenial homeowners, those who are used to digital solutions and want one for their paperwork.
Also small business owners, storing documents and easily retrieving them, possibly freelancers.

How you will promote it?
If homeowners, not sure.
If small business owners/freelancers, find communities of these and reach out.

What you think they will pay?
Homeowners, £5/mo?
Small business owners, £10–£50/mo? Depending on size.
Freelancers, £10/mo?

Who is the competition?
Evernote is used for this from what we’ve looked at, and small businesses may use existing business oriented solutions. Not looked at that space yet, know medium businesses + have options that cost a lot.

What is the smallest v1.0 you could do that someone might pay for?
Image upload, you take the image / scan and upload to our system for easy tagging and easy retrieval.

How are you different - why they might use you rather than a competitor?
B2C there doesn’t seem to be anything other than Evernote. B2B, unsure of competition, would need to investigate.

How long it is going to take to release v1.0?
Probably around 2 months.

Possible Business #3: Slack based employee engagement software
What problem you are solving?
Small–medium startups, especially remote startups, need tools to keep up to date with their employees current happiness, thoughts & feedback on the business.

Who is the customer?
Small–medium, preferably remote, startups.

How you will promote it?
We’ve got connections to some startups already through an existing product, and know people who know a lot of people in this space.

What you think they will pay?
Between £2-5/user/mo

Who is the competition?
Leo just released which is almost identical to our vision, and other, non-Slack based employee engagement software.

What is the smallest v1.0 you could do that someone might pay for?
A simple slack bot that allows you to set up questions to ask, asks them, responds with nicely presented data.

How are you different - why they might use you rather than a competitor?
Integrate with Slack, so are relatively frictionless for the employees. Although Leo has done that now too.

How long it is going to take to release v1.0?
Probably 3-4 weeks for a rough MVP.

There are some other options, like building upon FoundersKit, or making a tool for interacting with presentations on your mobile, but these are less clear on what we’d do here, and with the latter, whether anyone would want it. That one’s just one of those ‘lightbulb’ ideas with little grounding.

Thanks @Andy for prompting the questions here, Interested to hear people’s thoughts on the above.

Hey Fred!

In my opinion you shouldn’t start a company because you want to start a company. You should do it because you have an idea and you think it’s worth sharing and implementing. You don’t ‘choose an idea’, you have it and then it’s all about belief.
As an entrepreneur you’ll dedicate your time, money and energy so you better believe in your project, don’t you think?

Anyways, I’ll also advise you to register in an entrepreneur’s community (like “Ye! Community” for instance). It allows you to get some personalized advice, coaching, get in contact with other entrepreneurs from around the world and look for funding… pretty cool!

If you think you’re ready just go ahead, don’t be afraid to fail because it’s very likely to happen anyway and it actually teaches you a lot. Wish you the best of luck!


Hey Alexis :slight_smile:

Thanks for the response. I agree you need to be passionate about what you’re doing. I think it’s less about being passionate about an idea, and more about solving a problem, but that’s similar to what you’re saying.

I don’t necessarily think we need to wait until we have a massive passion though, I think it’s about working on areas that we find interesting, and seeing where it goes. That’s the route we’re taking anyways. Otherwise we’ll always just be waiting for the perfect passion idea and never do anything.

Appreciate the advice on the community there. For us we’re going bootstrap (at least to start with, but hopefully forever) so funding isn’t on the radar. Already a part of a mastermind and a few communities, but if I need more I’ll check that out.

We’re starting on the side whilst working full time, experimenting until we find something worth doubling down on. Once we’ve found what we’re gonna work on then we’ll quit our jobs and go all in.

Appreciate the thoughts dude :thumbsup:

Fred, great post - nice to see real ideas like that.

FlashTabs - you’re obviously on to something there (traction), that’s great! It’s not obvious exactly what way you’ll make money from it, but it seems like it should be possible with experimentation. Have you been working on FlashTabs over the past months?
Dropping ads on your users could be risky, I’d definitely dip your toe in carefully, especially when you’re making promises like ‘free for ever’. I don’t doubt that some people would pay some amount of money for prepackaged decks… or you could perhaps have sponsored decks from websites like (maths questions), or other learning/training sites?

Digital document solution - I got PaperPort with my printer/scanner, is that what you’re thinking, or are you thinking cloud based? Does this not already exist, besides Evernote? Personally I don’t like the idea of my docs going to the cloud - although I do use CrashPlan for encrypted cloud backups, so I suppose encryption and trust are what matter.

Just wanted to chip in because I thought you made an excellent post.

Thanks Jim, appreciate your thoughts.

Since the original post, we’ve left FlashTabs roughly as is for now, as I don’t think it’s going to be a big win for us financially. Focussing on other projects.

Released a new version of FoundersKit, and working on a SaaS app around a high level view on startup expenses. Kinda like Baremetrics but for recurring expenses. Testing that out and learning here.

We also wrote a small (12k words) ebook on learning to launch side projects.


My drawers are overfilled with papers I need to look at from time to time, like business taxes and communication with government (7 years to store), etc etc.

Ideally, I’d like to make a photo of the page with my phone, add tags and it is stored in a cloud and my local (like Dropbox does). It should do OCR for search and learn my tags, too - to offer them automatically in future.

Pay… I pay Dropbox $10/mo, so I do not see why document store could cost less.

Tho I would offer a freemium until N scanned pages - a homeowner should get dependent on the store first, and it will take probably a year.

Yes, OCR can be v2.

But make it scan from a mobile phone photo. Buying scanners are so … 1990.

You can partner with existing mobile solutions - I use CamScanner. It makes a photo of a page and converts it into PDF. You can organize those documents, and later add OCR capability.

I definitely think there’s potential in this, and really appreciate your thoughts! That said, B2C isn’t an area we really want to do, it requires huge volume and therefore funding etc, whereas we want to go bootstrapped.

So, I see potential here, but not for us I don’t think.

True. How about B2smallB?

I’m sure large co’s already have solutions in place.

I, for one, being a small business, could share my tax correspondence with my accountant the same way as I share my photos with my relatives.

I wouldn’t blanket-say B2C requires huge scale and funding… although that depends on the problem, solution, and goals of the founders.

There’s possibly something in there for small B2B. It doesn’t excite me much, but it may be something we test out a bit to gauge market demand.

Yeah you’re right, it was an over generalisation. I certainly think B2C leans more towards scale and funding, whereas B2B can work both ways, with it generally being easier to run a bootstrapped company B2B.

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I think those relationships and trends are correlations rather than causations.

Yeah could be. I get your point. I do think that if you’re looking to bootstrap, it’s, on average, easier to focus on B2B. Mainly because on average you’ll have businesses willing to pay money to solve problems more than consumers.

There’s obviously exceptions to the rule though.