The DEV Team

What are some of the biggest lessons you've learned as an entrepreneur?

graciegregory profile image Gracie Gregory (she/her) ・1 min read

The format of DEV's first official podcast, DevDiscuss, begins with an interview and ends with commentary from the community.

With season two of DevDiscuss coming soon (!!!), we want to know...

What are some of the biggest lessons you've learned as an entrepreneur?

This can include pitfalls, success hacks, points of reassurance for budding entrepreneurs, etc!

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Gracie Gregory (she/her)


Content Manager @ DEV. "You know what this sentence needs? An Em dash!" - Me to me

The DEV Team

The team behind this very platform. 😄


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In college I had a decently successful internet business, and I probably rushed to try new things instead of massaging what was working... because I had a fear that Amazon would crush me because of their efficiencies.

Looking back on those days, I'm impressed with how right I was in some ways. This was around 2010 so Amazon was not nearly what it is today (Its stock is about 25x the price 😬), but I was right to be concerned about how well they were doing and how big of a beast they'd become.

What I was wrong to think is that they'd be able to crush me if I wasn't ruthlessly efficient myself. In fact, when you're small you don't need pure efficiency because you can be more creative and try more things more often. Had I just kept methodically working on the business it would have kept growing and turned into a big success. I tried to move too quickly and get big, and in doing so just kind of burnt out and let this project fade away.

Lesson is... You're not in a mad race against the big guy. You can slowly build up your value offering and you'll be fine if you stay committed and keep shipping.


You're not in a mad race against the big guy.

This is huge and something everyone needs to know. People stop themselves before even trying because of a perceived obstacle that may not even exist. Or, as you said, they try to compete against time, when they have all of the time to learn and grow.

I've heard that many things fail just because people didn't stick with them long enough to see the rewards.


This is why I don't fall for the antitrust stuff. If a company is wildly successful, there's always room (at least in a mostly free economy) for a little guy to make a nice chunk of change alongside (and possibly get bought out by) them for an even bigger chunk of change (though maybe be careful if Amazon comes along talking about acquiring you, and definitely don't let them peek at your tech stack).


Thank you for sharing.
I'm glad to see you didn't give up and moved on to create this wonderful community.

  • Doing taxes yourself, you are standing with one foot in jail already. Find someone that does taxes for a living and don't skimp on money in that regard. A good tax advisor easily earns his money back and then some.
  • Laws are brutal, don't try to understand them, find someone that does and pay them handsomely
  • Insurances are important, it's better to have one and not need it than need one and not have it
  • Employing people drastically increases your work, the benefits of previous points add up here too. The moment your first employee starts his work, new laws and tax regulations may apply. You'll be happy to have a tax advisor and lawyer on hand to prepare you for the changes.
  • Invest in your employees and treat them as your equal, money should be your very last concern
  • If you can legally cheat the system and get your money back, going back to taxes for example, don't feel bad, just do it
  • If you can save money, most of the time you'll regret doing so. Money is just like materials for a workshop, materials that sit around for too long go bad or not having enough of them can and will bite you. It's just money, a resource, use it to generate more.
  • That being said, have a rainy day fund. Being able to pay the bills of, for example 3 months, without income is going to help you sleep better at night. 3 months might not sound like a lot, but considering the current global pandemic, 3 months can save your company.

I can probably think up more, this is just off the top of my head


From my experience this is not true. Tax consultant did not help. Lawyer was terrible. Employing people does not guarantee benefits. In the end I actually needed to do most of the work by myself, and was successful. But you need to consider a lot of time for researching taxes/laws (instead of third party) and automatisation (instead of employees). Saving money is highly important to compensate unexpected costs.

Insurance, yes, you should always have a health insurance (which is not a choice but required by law in most EU countries).

Jm2c from Europe. 🙂

  1. Everyone starts at zero.
    Don't compare yourself to others who already are successful. Remember they started at zero, too.

  2. Treat every setback not as a setback but as a learning opportunity.
    When starting, everything is chaotic and you feel like you don't know what you're doing. It's okay. You don't know what you're doing and neither did anyone else when they started. It is really in this chaos where you can learn the most.


I learned that losing focus from the most important things is very, very easy. There's a reason a lot of people insist on making a plan and sticking to it. It's too easy to get side-tracked by "a cool idea" that you can add and wake up later that you wasted 6 months for a random idea.

2nd lesson I learned is that the team you work with is more important than the product. You can't do it alone and finding the right people with the right skills (mostly those that you lack) is not a trivial task.
Make sure you start with at least one or two more co-founders and ... delegate, delegate, delegate!


Be sensitive to the market.


I think "get out of the building" is the most critical advice (do it virtually these days!). Solve a real problem, and find people to react to your solution. Time spent anywhere else is mostly wasted until you have a real customer feedback loop.


Yup. It's great to anticipate wants and needs your customers might not even know they have, but useless if you don't know (and provide) the wants and needs they do know they have.


Never underestimate the importance of the right co-founder(s) (or lack thereof). There's a lot more to it than just being someone you like and trust.

They need to be willing and able to do the things you can't or don't want/have time to do. If they can't/won't and aren't willing to learn how, you're better off without them.

If you came up with an idea together, you either need to be grownups and figure out who does what, bring someone else on to help (heeding the warnings above), decide how to dissolve, or buy the other(s) out and keep going (or let them buy you out).


I learned that it's important to validate an idea before you put a product out! I released my first digital product earlier this year which did really well because of the target audience and the subject matter; it met a real need. I released a second digital product that has been doing fine but is for a more niche audience, and I released a translated version of my original product which has sold only a handful. If I could do it all over, I would not have moved forward with the translation!

Another thing is to give a lot of free value. Everyone isn't your customer and everyone won't end up buying what you're selling, but consistently giving away free knowledge will help you attract the right customers down the road. It sets you up as someone knowledgeable in your space and you become known as someone who wants to help people than sell them something they may not want.

Finally—track your business expenses religiously! I'm doing everything manually via a huge spreadsheet to get into the habit of bookkeeping. I'll delegate this task eventually, but for now I find it to be incredibly important to know how much is coming in and how much is going out every month.


You don't need a big Twitter/Social Media audience to be successful. Treat it as any other marketing channel. Sometimes people become demotivated when they see that everyone that seems to be successful already has 20k+ Twitter followers. The thing is, you chose that bubble yourself. And if you think it might be the right marketing channel for your business, building up a decent audience isn't that hard if you are consistent.


After more than a year of bootstrapping Spike.sh, here's a small gist 👉

  1. Choose your failures - Really difficult to get good at this. Select a path which is less expensive and less hurtful

  2. Play on your strengths EVERYWHERE - If your strength is prioritising or customer support obsession then play that card everywhere from your landing pages to your email copy. Your visitors will immediately value your strength and resonate with you