THE BLOG
05/07/2013 03:01 pm ET | Updated Jul 07, 2013

A Field Guide to Solo Entrepreneurship

It's now easier than ever to start a company -- even as a single founder, it's not unimaginable that one could hack his or her way to success in the matter of a few years, and sometimes less.

Web languages and technologies are more accessible than ever, with tutorials, classes, and resources just clicks away. Fundraising has been democratized, with sites like Kickstarter and Indiegogo enabling users to validate demand for their products easily, all while pulling in dough to get started. And coworking spaces, hackathons, incubators, accelerators, and business competitions are all the rage, offering would-be entrepreneurs bounds of opportunities to get started.

There's a special type of entrepreneur, though, who chooses to go the road alone. These so-called solopreneurs manage to pull off every angle of business as lone wolves. They code, promote, land partnerships, pull in users, generate press, fund their own businesses, and do everything else in between.

I spoke with six solopreneurs, all insanely driven and passionate about their work, to understand how others might be able to finagle themselves to solopreneurship. From what I learned, it doesn't take a superhuman, but instead requires an immense capacity to learn and undying curiosity to actually follow through.

Bootstrap With Care

Once you've got the startup bug, it's tough to put your idea on the backburner and continue on with life. Unless you've got enough money in the bank to last a year or so, you'll need to consider the best ways to finance your new project.

Bidsketch Founder Ruben Gamez says that his full-time job helped him cover living expenses until Bidsketch was able to replace his salary. With a family, Gamez was very risk averse and had to make sure he was cash flow positive before quitting his job. There's no shame in working nights and weekends until you've gained traction. For Gamez, that was about a year and a half after launching, he says.

For Angela Wang, founder of Republic Spaces, the extra cash comes in through her web development company, where she says she "does quick websites to cover some of my expenses."

Open Exchange Rates Founder Joss Crowcroft says all solopreneurs should develop a baseline skill of hustling. An enthusiastic engineer, Crowcroft got his start in web development in college when his childhood love for building things was reignited through a website project, which launched him into 14-hour days of coding euphoria. He says that building stuff has always been the easy part for him, but selling his work is a bit trickier. Hacker News, smart friends, and conquering his irrational fear of "asking for money" have gotten him over that hump, he says.

Don't feel awkward asking customers to pay for your product or clients to fork up the money they owe you. "I've learned that a big part of being professional is just being comfortable asking somebody to pay you for things, for the value you provide," Crowcroft says.

Have a Support System

Michael Horn, founder and CEO of Craft Coffee, says he started building his business using money he had saved. Then, he lived off credit card debt until he was absolutely broke. And finally, he turned to his support system, and a friend of his invested enough money to cover Horn's rent for three months. After that ran out and Horn had made good on his promises with hard work, his friend renewed for another three months of rent.

It's not best practice to consistently mooch off of family and friends, but when times get tough, many entrepreneurs lean on those closest to them for support.

Whether it's about money, feedback, or simply a little food on the table, your support system will be there if you've built it with love and care. "I am very thankful for friends, ex-boyfriends, [and] past clients, who appreciate me enough to feed me yummy food sometimes," says Wang.

Erez Pilosof, founder of Hopflow and Chatflow, says that solo startups are exponentially more difficult to pull off than traditional tech startups. "You must have amazing focus, discipline and strong character to push against tremendous odds. With only yourself to count on from a business perspective, be prepared to go through ups and downs, good times and bad. A tip on the personal side: You must have the full support of your loved ones to be successful." Words of wisdom to live by methinks.

When business get tough, though, Gamez recommends reaching out to other solo founders for advice. "One thing that's been a huge help for me is having an amazing team of advisors. They're three successful solo entrepreneurs that I respect and have become great friends with," he says. "If you're planning on building a successful business, it's extremely helpful to form relationships with successful entrepreneurs that you can learn from. Learn as much as you can by asking questions and paying attention to how they do things. You can give value back by taking action on their advice and being as helpful as you can."

Building a "mastermind group" is another strategy for getting outside of your comfort zone, says Crowcroft. "With no team to challenge you, you'll repeatedly fall back into comfort zones -- for me that's excessive coding -- and forget the hardest and most uncomfortable tasks are the ones that force you and your business to grow," he says. Get a group of likeminded people together to challenge each other to do their best work, he advises. The result will be newfound accountability and a great opportunity for cold, hard truth.

Hack Your Skills

Some solopreneurs come in with coding backgrounds, others with business backgrounds. The good news is that intellectual curiosity, constant learning, and hard work can help anyone bridge the gaps between the two.

Horn, for example, is a self-taught programmer. "I literally locked myself in a room for six weeks and taught myself to code in Ruby on Rails," he recounts.

Wang, though, picked up a number of skills from jumping around in her career. After studying architecture and product design at the Parsons School of Design, she picked up stock trading, dipped her toes into the Internet marketing world while working for a large ecommerce company, began developing mobile and business development strategy for Fortune 500 companies, and eventually started her own web development company, all before founding Republic Spaces, a marketplace that connects underutilized retail space and designers interested in short-term retail initiatives.

Wang's extensive work experiences set her up to have nearly all the skills she needed for building Republic Spaces -- the only thing she really learned especially for the company was Rails, she says. "I have mostly done PHP work in the past. I decided to learn Rails for Republic Spaces, as it's rumored to be highly productive, and it truly is. I actually learned Rails last August through Code School and Railscasts and finished developing the app last November," she says.

A founder's work is never done, though. Wang says she's absolutely horrible at public speaking. But of course, she'll be taking public speaking lesson in the near future, she confides.

Consider Hiring Others

For those solopreneurs lucky enough to build a business that gains massive traction, and thus requires the attention of more than one employee, hiring becomes a part of the conversation.

Craft Coffee, founded by Horn in 2008, hired its first employee in November 2011 and is now a core team of three, currently in the market to hire more.

"The moment where you go from being completely alone to having help is an incredible transition," says Horn. "There's a point where if employees believe in the company's vision, you'll hear them talking to people in the office and explaining what we're all about. And you just stop and think, 'Wow, this thing is bigger than me now. I can't believe it!'"

Crowcroft, still working as a one-man shop, says he hires freelancers and contractors from time to time and prefers to emphasize his strengths, instead of fixing his weaknesses. He focuses on making his product as great as possible and defers to people smarter than him for advice on other matters. He's always liked the expression, "If you think it's expensive to hire a professional, wait until you hire an amateur," and seems to live by it.

Crowcroft says he'll eventually need someone for customer service and technical support and finds outsourcing to be a bad plan for something so crucial. He plans on reaching out to his network for starters to find that special someone.

Final Thoughts

The beauty of entrepreneurship is that you have the opportunity to do what you want to be doing. Horn recommends that if you're an aspiring entrepreneur, you seek our your dream job, that sweet spot, "that place that combines your experiences and interests and skills." Once you've found that, it will all come together, he says. "That's the magic of startups that draws people to them and draws people to founders, too."

Keep learning, nothing is complicated once you understand it -- and if it is, it's a great opportunity to simplify," says Loren Brichter, founder of atebits, Letterpress, and Tweetie, his first app which was acquired by Twitter in 2010. "Think about what you're doing. Remember that money is a side effect, not a goal. Take advantage of being small... The beauty of software is that it's a massless, incredibly pure form of creation. A single mind with the right set of skills can conjure something valuable."

Finally, Wang says to take a queue from Nike and "Just do it."

"Have utter confidence and faith in the fact that you can do it as a solopreneur," she says. "Just build something, and if you have something solid, you will attract all the right people to make your company successful. Do not doubt yourself for a single second."

Images courtesy of Shutterstock, including worn leather boots, miniature helpers, business woman, and jobs photos.