: Bootstrapping + Lessons Learned: Rookie Mistakes + Beginners Luck

Like many entrepreneurs, when we began what we now refer to as “the EssayJack journey,” we were focused on the product. In our case, not only were we developing a new product, but we were forging new ground by developing a whole new product category.

We made the conscious decision to take the big risks on our own shoulders, because we were inventing something new (something that we wanted, something that our friends and colleagues wanted, and something that filled a gap in the market…) but without any clear competitors, it was hard to know if the market really wanted what we were creating.

In the earliest days, we were unsure of whether or not our product was something the world even wanted (beyond our test circle of 200 MVP users) so we felt responsible to take that early risk on ourselves. We thought: nothing ventured, nothing gained. We figured it made the most sense for us to build the product that would be faithful to our vision, test it in the market, and upon clear validation, grow based on revenues, bank loans and some investment.

That was a great plan but it failed to take into account a few key things that I’ll share as some of the lessons learned:

  • Product development always takes longer and is more expensive than you might think. Even with the best teams and tightest budgets, you run the risk of cannibalizing all other budget line items just on tech.
  • Once you get the validation from the market, things MOVE FAST. You won’t have time to backfill all those positions that you didn’t have money for at the start because your customers will be coming fast and furiously and you will be running to catch up to the demand.
  • Expenses will outstrip revenues no matter what (at least for the first while.) Running a tight financial ship is great and important for good corporate governance and fiscal management going forward but being too lean can lead to missed opportunities.
  • Fatigue is a real thing. Really. As an entrepreneur, it is tempting to do the job of 10 people. Sweat equity by a dedicated founder can achieve a lot. However, your sweat equity is a nonrenewable, exhaustible resource. At some point, burnout is unavoidable.

Despite making some of these rookie mistakes ourselves, and feeling like we’re always playing catch up, we’ve had some extraordinary good luck in finding the right investors who believe in us and the vision, bankers who have been patient in extending our lines of credit, and customers, partners, and clients who have been collaborators with us as we figure things out along the way.

Because of our good luck, we’ve been able to overcome some of our rookie mistakes, but I would say to any young entrepreneurs getting started that deciding when and how long to bootstrap, when to invite investment, what sort of investment you are looking for and how to manage your growth are all really important questions that shouldn’t be overlooked while you focus on building your product.

Oh, and if you’re starting your own entrepreneurial journey, I wish you GOOD LUCK and mean it. Luck can make all the difference!

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