Melissa Kwan

I love bootstrapping, but it comes with tremendous difficulties. These are the 11 biggest challenges we face at eWebinar: 😰 

1. We're forced to make tradeoffs.
Every dollar going to the wrong thing is a dollar not going to the right thing. We're constantly choosing between what we need to do now versus what we can push off until later.

2. Growth feels too slow.
Profitability can’t come fast enough when there’s a zero-cash date looming. When you’re spending more than you’re making, even 30% growth from the previous month seems miniscule.

3. We’re too small to matter.
We can’t offer enough reciprocal value to ignite meaningful partnerships. We don’t have the mailing list or brand recognition for bigger companies to get excited about.

4. Media coverage is non-existent.
You can be building a better product than your funded competitor who’s on the cover of Techcrunch but nobody will cover you because you’re not clickbait worthy. And we can’t spend money on sponsorships and a PR firm.

5. We’re always fighting.
Without the stamp of approval and credibility that comes with VC funding and media write-ups, we have to fight for attention, trust, and validation from everyone: prospects, customers, and partners.

6. Customer support is perceived as less reliable.
Some companies have turned away from working with us because we don’t offer enterprise level support. Truth is, we bend over backwards for our customers because every dollar we lose hurts. We’re more responsive, provide quicker resolutions, and implement customer feedback more than most big companies. And yet…

7. Big companies can’t work with us.
These companies are bound by compliance requirements. They want custom contracts, GDPR, SOC 2, security reviews...things that are too expensive for us to invest in now.

8. We’re never doing enough.
Everything we read tells us we should be doing all these things that we’re not doing. It always feels like we're screwing up and going off-track. But we are already doing the best we can.

9. I’m the last to get paid.
I’m at the bottom of the salary totem pole. Every time I’m about to pay myself, another expense comes up and I get bumped. After working so hard for years to pay the company’s bills but never my own, it can be pretty demoralizing some days.

10. The struggle was much harder at first.
Compared to our VC-funded counterparts, we struggle more in the first years because we need to be scrappy in both our professional and personal life. Good news is, our struggle ends the day we hit profitability.

11. It's hard to sleep well at night.
All these things compound to subconscious anxiety that comes out in my dreams almost every night. I can’t remember the last time I had a great night's sleep in the last decade.

Bootstrapping is a slog.

But you know what else is?
✅ Building a VC-backed startup.
✅ Waking up to a job you hate everyday.
✅ Regretting never chasing your dream.

Everything is a slog.

Choose the slog that excites you the most.