Being Honest With Yourself (When Things Aren't Going Well)

I really wanted to be a founder of a successful startup (where successful to me means the company can pay its own bills, and pay employees well). However the reality hasn’t matched my ambition and I’ve decided to find a job like a regular chump.

I assumed that with work ethic, skills, persistence, and plenty of trial and error I could eventually find success. That hasn’t happened, and I’m nowhere close to making that happen. Being good at computers and working hard doesn’t cut it.

The truth is, to be successful, you need 2 things: luck and connections. Connections are the piece I lack, as I’m naturally bad at relationships. Nobody has invited me to any VC happy hours.

False Hope #

On raising money: Early on in my wantprepreneur journey I assumed it would be easy to raise money. I’ve heard that people are clamouring to invest in people like myself. In practice, however, I found that not to be the case. VCs would ghost me, and after sending hundreds of emails I realized you can’t email your way into a meeting.

VCs want you to keep grinding away, and they will wait until they have no choice to invest. No one wants to be the first to invest. They also don’t want to invest in unknowns. The VC model works best when there’s perception of success (actual success doesn’t matter, VCs make money whether companies succeed or fail). The data suggests that the old adage “it’s not what you know, but who you know” is often true in startup funding.

On finding product market fit: There’s a lot of mythos surrounding the elusive “product market fit”, but one thing I’ve learned from my years working in computers is that you can’t really get there unless you a) have a lot of resources and b) are really good at marketing.

Even the canonical example of product-market fit—Dropbox—had an extraordinary marketing strategy. Their viral referral program that gave users free space for inviting friends is legendary, but what’s less discussed is that they had $1.2M in seed funding before launching that strategy¹.

On building great products: It doesn’t matter how great your product is if nobody knows about it. A lot of enterprise software companies have bigger marketing and sales departments than engineering because at the end of the day sales and marketing matter more than the quality of the product.

Slack, often cited as an example of product-led growth, actually spent heavily on traditional marketing. Their “love letters” billboard campaign in major cities cost millions. The narrative of “if you build it, they will come” is largely a Silicon Valley fairy tale.

Feeling Hopeless #

Scrolling through my LinkedIn feed I can see how a number of my former colleagues have managed to go out and raise large amounts of venture capital. I’ll admit, I’m resentful, but I’m also happy for them.

I know what I’m good at: building products, getting shit done, shipping code, making things happen. You’d think those are the things that matter when it comes to building a startup, but the truth is that those things are only secondary. The most important thing is being able to convince people that you can do these things (or find people who can), and also being able to get the attention of people who either want your product or want to invest.

Silver Linings #

It’s worth noting that there are successful companies that haven’t followed the VC playbook. Mailchimp reached a $12B valuation without ever taking outside investment². Basecamp has been profitable for 20 years by focusing on customers, not investors. These “bootstrapped” success stories are less celebrated but perhaps offer a more realistic path for those without connections.

What’s Next? #

For me at least, I’ll stick to what I’m good at in the meantime, and let someone else deal with the fundraising and marketing. I think for anyone like me, you’re more likely to succeed by joining an existing startup and working your way up from there.

There’s no shame in pivoting your approach. Many founders who fail at their first venture go on to found another company. The skills you develop along the way aren’t wasted—they’re investments in your future success, whatever form it takes.

By being honest with myself about my strengths, weaknesses, and the realities of the startup ecosystem, I’m better positioned to find a path that actually works for me rather than chasing someone else’s definition of success.