How To Survive The "Trough Of Sorrow" As A Solo Non-Technical Startup Founder

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And then my co-founder and CTO in Julia Grace joined my startup. Having a co-founder is infinitely better!

By Tracy Osborn (Founder, WeddingLovely)

In the last year, I’ve gone from building a random side project (after finding a co-founder ultimately failed), to running a revenue-generating company which just finished the F11 batch of 500 Startups.

I’ve done all of this as a solo female designer first-time entrepreneur. I’m building WeddingLovely, dedicated to making wedding planning easier and supporting independent wedding vendors.

Looking back on the last year, there are several big things that directly contributed to the success I’ve had thus far. Before I dive into my story, I’d like to note that having a co-founder is better than not having a co-founder, but doing it by yourself is 1000x better than giving up (and 200x better than continuing with the wrong co-founder).

My tips for surviving and being successful as a solo founder:

Be endlessly curious and creative.

I’m a designer, but building a revenue-generating web app takes marketing, development, and a slew of other skills that I either did not specialize in or haven’t had any experience with. If I restricted myself to just being a designer and outsourcing those other aspects of the business to contractors, the company would grow slower. Not only would I be much, much less invested in how well my company is doing, but I also would have run out of financial runway long ago.

The natural contrary point to this is: wouldn’t it go slower if I, the non-expert, worked on it, rather than an expert contractor? On paper, perhaps — but contractors, by definition, do not care about your product as much as you do. As soon as the project is over, they’re moving on. You’re going to have to maintain everything that’s built after anyways, so might as well build it from the ground up yourself. Doing it yourself is also great for figuring out what your true MVP is, and figure out how little you can build to get your product launched and in front of customers faster.

Learning the basics of any skill isn’t hard. Software development looked particularly challenging, but I took as many shortcuts as I could in order to get my first product out. When WeddingInviteLove launched, I honestly didn’t know why most of it worked. But it did work, and that’s what matters. And in the last year, I’ve become 10x ?x the developer, continuing to learn while iterating on my application.

Fill the emotional gap of a co-founder.

Being a founder means that when things get shitty, things get really shitty — your startup is your baby, and being a founder is even harder when things are going badly. It is very easy to be discouraged when it looks like you’re going downhill, and discouragement is the worst possible thing to happen to a solo founder. Extremely important: make sure you have at least one seasoned entrepreneur friend that you can rely on to be your sounding board.

Share elation at things going well, someone to listen when you have bad customers, a shoulder to lean on when mistakes are made, and most importantly, a calm voice to tell you that when you feel terrible and it seems like your company isn’t going anywhere, that things really aren’t as bad they seem. These are all things a co-founder would do for you, and it’s vital that that you have someone to fill that gap.

Public shoutout to @shazow, YC S10 (with IMoveYou) and founder of SocialGrapple (acquired by Google), who has always been there for me.

Be stupidly persistent.

Don’t take no for an answer — at least, don’t let it discourage you. Being a solo founder means that people will naturally scoff at you (“Why can’t you convince anyone to found a company with you?”) I’ve been denied from Y Combinator twice, and have had more angel and VC rejections than I can count. The fact of the matter is, I enjoy what I’m doing and I’m going to keep on trucking, no matter the number of rejections.

Being persistant helped me seriously speed up my own trajectory. Being naturally passionate about the idea of designers as founders, I was very intrigued when I heard about The Designer Fund. Not knowing Enrique personally (the founder), I made it my mission to meet him, get to know him, and hound as much as possible to be considered for The Designer Fund.

I’d show up to random events that I knew he was attending, persuaded mutual acquaintances send multiple email and personal intros, and kept following up as much as possible myself. I was accepted, and confirmed that my persistance was crucial in their consideration.

Getting into The The Designer Fund set me up with a $5,000 grant as well as granting me two advisors: Christina Brodbeck, the founder of theicebreak and the first UI designer at YouTube; and Ben Blumenfeld, the design lead at Facebook (see below point about surrounding yourself with people smarter than you).

The single best benefit of The Designer Fund, however, was scoring an interview with 500 Startups. Paul Singh was already a fan of what I’ve done and had seen my previous articles through Hacker News, and accepted me into the program (then he proceeded to proclaim that I’m a “cockroach” since I’m persistant and nothing will kill me. Love it.)

Getting into 500 Startups officially changed my directory of WeddingLovely from a personal project to “I can make this really, really big.” Not to mention the $50k investment money, access to the 500 Startup’s network of founders and mentors, introductions to investors, learning to pitch, and multiple educational talks a week (such as startup accounting — how basic, yet how vital).

I knew getting into The Designer Fund was vital, but I had no idea where it would take me. I wouldn’t be where I am right now if I didn’t get in.

Befriend people smarter than you.

My #1 skill is in web design. But being a solo founder, I also have to be the lead engineer, lead marketer, server admin, and every other vital role in a tech startup. I need to be an expert in fundraising, even though I haven’t raised a cent before. I have learned so much over the last year because I have surrounded myself with people smarter than me, who are okay with me asking stupid questions.

Make friends who are fantastic engineers. Make friends who are seasoned entrepreneurs. Don’t be prideful — ask stupid questions and learn from their advice.

This is the biggest obvious advantage to being accepted into an incubator program such as Y Combinator, 500 Startups or TechStars: Instant connections to people who are really, really smart.

Focus on revenue.

If you’re a solo founder (and in my case, first-time and non-technical as well), fundraising is going to be 10x (perhaps 100x) harder. It’s easy to hear stories of seemingly silly startups raising 500k seed rounds with just an idea and think that fundraising isn’t that hard — that all you need is an idea and a shoddy MVP — and the cash will be magically falling into your hands.

Chances are: you’re not lucky, you’re not going to raise money, and fundraising is going to a bitch of a process and severely depressing. It’s hard to pitch your company to angels and VCs and get “meh” in return — not to mention, if you’re a solo founder and you’re fundraising, you have no time to work on product, and your progress is going to stagnate while you’re trying to raise money.

Find a product where you can work hard and bring in revenue. It’s much more rewarding. I’ve heard good things about Amy Hoy’s 30×500 class, which sounds like a good hand-holding class for anyone wanting to jump into a revenue-building project.

It’s also surprising how easy it can be sometimes to convince a stranger to pay for your product.

Revenue first is key when you don’t have a co-founder. I remember when I first added paid accounts to WeddingInviteLove, and being completely baffled when ~10% of my existing customers upgraded — and my conversion rate has stayed at 10% ever since.

Keep looking for a co-founder.

Just because you started solo doesn’t mean you always have to be solo — continue building your company and the right person could show up.

Don’t force the process, but it can happen, and it’ll make life way easier once you have someone on the team that you trust and know is a great fit for what you’re passionate about. Start looking early for a co-founder, and keep in mind people that you’ve known for awhile who are unavailable — keep them informed on your progress and a few months down the road, they could become available and join you.

Why is this my last point? Because Julia Grace, a brilliant engineer and my long-time friend, just joined WeddingLovely as CTO and co-founder. Rock. On.

I could have kept going as a solo founder, but having a co-founder is infinitely better than not having a co-founder, and I’m sincerely excited about what we will build together.

Conclusion

Be scrappy, be creative, find the all the shortcuts you can take, make revenue, and just keep on building. I have the best job in the world, and I am so glad I jumped into building a company on my own and started building my own future rather than waiting for the right co-founder, or giving up and becoming another employee. It’s been hard, but I have come so far and learned so much in the last year, and I wouldn’t change things one bit.

This post was originally posted at Wedding Lovely’s blog.

About the guest blogger: Tracy Osborn is the Founder of WeddingLovely. She is the creator of WeddingInviteLove, a curated directory of wedding invitation designers, and spends her time working on wedding-related web apps and communities. Prior to founding WeddingType, Tracy freelanced design and front-end development for startups. Offline, Tracy tries to spend as much time outdoors as possible, hiking and biking around the Bay Area. Follow her on Twitter at @limedaring.