Lone wolves vs teams – is it even possible today to create a successful startup alone?

What do Flappy Bird, Urban Dictionary, and Plenty of Fish have in common? That’s right, all of them were built and launched by only one person.

These are not the only examples of success, though. DuckDuckGo, Instapaper, Todoist, Newsblur, and many other startups share that same story. Naturally, their examples inspire thousands of new startup founders every year.

The success of famous single-person startups excite the minds of many aspiring entrepreneurs who think they can take on the world all by themselves. And they may be just right... if they have the right skillsets, that is.

Taking a closer look at their stories will draw for us a better picture.

The good

Plenty of Fish

In 2015 Markus Frind sold one of the biggest dating platforms in the US, Canada, Brazil, and UK for $575 million dollars. He founded Plenty of Fish in 2001 and has been working on it alone for 7 years before hiring his first full-time employees.

Of course pof.com owns its success in part to the flawed competition. Most dating websites during that time had atrocious UI and a lot of paid features.

Markus decided to make a completely free dating service that – plainly speaking – didn’t suck so much. His new side project ran off his home PC and didn’t earn any medals for being pretty. Even now Plenty of Fish is simplistic, even primitive – but Frind doesn’t want to change anything.

I don't listen to the users. The people who suggest things are the vocal minority who have stupid ideas that only apply to their little niches.

Markus Frind in "How Plentyoffish conquered online dating"

Plenty of Fish accumulated popularity slowly. Markus was hard at work optimizing his website for Google and searching for opportunities to earn more ad money. At the same time he greatly improved matching algorithms and optimized POF even further.

POF gained one of the smartest matching mechanisms on the Web and as a result the audience quickly grew larger.

Frind essentially single-handedly achieved the wet dream of any businessman: he managed to combine low operating costs with an ever-growing active audience that was willing to recommend his website to other people.

10 years later, Plenty of Fish remains one of the largest dating website on the Web with 50,000 users signing up for the service every day.

Urban Dictionary

Aaron Peckham owns one of the biggest websites on the Internets where any word has at least one sex-related definition. This is a joke (I guess).

This famous dictionary of modern slang grows every day thanks to regular contributions of its dedicated members.

Aaron is the only founder and owner of Urban Dictionary. He founded the website alone in 1999 as a joke parodying other respectable online dictionaries. But Aaron soon discovered that people actually used it a lot. New slang words appear every day and users used Urban Dictionary to quickly look up any word they found.

In 2008 Peckham finally left his job at Google to work on Urban Dictionary full-time.

I just wanted to work on one project that represents me.

Aaron Peckham in "A lexicon of instant argot"

In 2010 Urban Dictionary kept records of more than 5 million definitions. In 4 years this number grew to 7 million spanning 30 languages with contributions from all over the world.

Even though Urban Dictionary doesn’t generate gazillions of dollars every day the author lives comfortably within the niche he discovered.

Flappy Bird

In 2013 in just 9 months a young game developer from Vietnam made more than $3 million dollars in ads from his viral app, Flappy Bird.

Dong Nguyen made his unbelievably addicting game in less than a day and released it first for iOS and then for Android.

Although it’s hard to say how the game initially gained traction, they say a number of Youtube-famous gamers with a dedicated following contributed heavily to its popularity.

Internet is surely a strange place and Flappy Bird is a good example of its random and finicky nature.

The bad

Findory

2001-2003 was the period when the traditional media companies started to separate their offline and online presence and focus more resources on serving Internet users.

In 2004, around the same time when Digg was founded, Greg Linden announced the launch of his own content customization platform, Findory. Findory was designed as a smart self-learning news aggregator that tailored its content according to the articles you already read.

In 2005, at its height, Findory served more than a 150,000 articles a day to 3,000 users.

Worrying about his limited financial resources and inspired by the initial success of the platform Greg decided to continue to do everything himself. His one-man army lacked consultants, marketing, finance, and business development experts.

Greg tried pursuing VCs who were too afraid to invest in a high-risk startup. A single-person team did not resonate well with venture capitalists and investors.

I re-learned the importance of a team, one that balances the weaknesses of some with the strengths of another. As fun as learning new things might be, trying to do too much yourself costs the startup too much time in silly errors born of inexperience.

Greg Linden, "Starting Findory: The end"

Greg hesitated to turn to full-time hiring as he was afraid it would eat up his runway too quickly but instead tried to do everything himself. Following the decline in popularity, he finally decided to close the startup. In 2007 Findory was acquired by Microsoft.

College Inside View

In late 2013 College Inside View was founded as a one-man team startup that aimed at helping students choose their new school better by reading reviews and honest opinions of people who were already studying there.

Adam Zelner was a fresh graduate of Fullstack Academy and saw first-hand how hard it is to choose the right school when so little information is available online.

Adam built a crowdsourced platform that offered insight on more than 300 schools across the US. The problem was that very few people were really interested in answering his questions for free.

Even with the added financial incentive (Adam paid 1 dollar for every posted answer) the company managed to collect enough reviews for only 1% of all target schools.

Among other problems Adam was very new to programming. He vastly underestimated the challenge of designing, building, and maintaining a complex online system all by himself. Without a team to back him up with critical knowledge the development process almost slowed down to a halt.

I underestimated the difficulty of the coding. I was bad at coding. I had a vague understanding of HTML/CSS/JS and had started the site right after spending a few weeks learning Rails. In reality, the coding was harder than I expected and I spent way too much time trying to hack stuff together.

Adam Zelner, "A case study of a failed startup"

But even after building his new platform Adam had another big challenge before him. Without any traction it was hard to convince VCs to invest in the startup.

Adam was quickly running out of money. Unable to pivot he had to close the business in 2015 citing lack of investor interest, lack of traction, and difficulties in validating the concept early as the main reasons of College Inside View’s demise.

Bitshuva

BitShuva was founded by Judah Gabriel Himango almost by accident. This aspiring radio station software startup was born out of a small side project Judah was passionate about – he wanted to build an online radio station to listen to the songs of his religious community.

He discovered that there were very few ready solutions on the market and decided to build something new all by himself.

After he finished creating the station other cultural communities started approaching him about a similar product – from local bands to East African pop musicians. So without a single effort Judah discovered a great customer base that needed uniquely designed radio stations and was willing to pay him for his software.

The first mistake of the startup was a short-sighted charging model. Judah only asked for a $1000 fee to build, deploy, and maintain the station and as his user base grew he eventually discovered all the time-consuming activities he needed to perform to keep customers happy.

Smartphone support, cross-browser use, new feature requests, and bug fixing creeped up on the founder without giving him a steady cash flow. The customers felt like they already paid enough to demand free support and updates yet BitShuva earned only a few hundred dollars a months and became unsustainable.

I was unable to devote enough time to developing radio software [balancing] between my day job and my family life. I simply can't devote enough time [to BitShuva].

Judah Himango in his farewell email

Instead of working on his startup full-time and rebuilding the business model Judah Himango decided to close the company and make his software open source.

You are (not) alone

The idea of starting out on your own may be a controversial one but a lot of people do find it appealing. So after taking a look at all these stories let’s discuss more in-depth the pros and cons of doing it with a tough team of one.

PRO: Running lean makes your operational costs extremely low

The team may add a lot of value to the project but there are multiple overt and covert costs of maintaining even a few employees. You need to dedicate your time to hiring and bookkeeping, you pay salary and employment taxes, provide office space, equipment, and benefits.

If your budget is thin, building a team may not even be an option. Instead look into contracting out the work that you cannot do yourself. This is an easy way to save resources and spend your money in a more controlled way.

CON: Filling in critical positions is crucial to success

There are only so many hours in a day. After the initial stage is over make sure your business continues to grow. Hire decisively when you feel the time is right for expanding and fill the roles that give the most value to your product.

PRO: Avoiding co-founders will make you the sole owner and decision-maker of the company

When you have a vision it is often hard to communicate it right to other people. You will probably encounter different opinions and views on the same issues. Do you really need that additional challenge of convincing your employees and cofounders that you are right? What if they don’t listen? The founders usually share company equity and have the same power of vote. Are you sure you want to fight for every decision you make? After all, according to the statistics, 20% of startups experience founder split.

And why do you even think that giving a part of your company is ever a good idea? The only time you absolutely need a co-founder is when you lack a vital skillset to launch your product into the world and don’t have the money to contract the work out.

CON: Being jack of all trades will make you master of none

People tend to have specialized skillsets that roughly define them as either more business-oriented or tech-focused. Both skillsets are crucial to the success of your startup. You need to have a portion of both to build the product and market it successfully to the investors and the consumers.

PRO: Being in control, staying in control

A single founder owns 100% of the equity of their business and will usually give only 30% of equity in the first round of investment while two founders who have 50% each will end up with 35% of equity after the first round of investment. So even the first round will significantly aggravate their ability to make independent decisions.

CON: Investors prefer to give money to a team rather than a one-man business

Angel investors and venture capital firms look at the team more than they look at the project. During the development process your vision and ideas of what is the best product for the market could change dramatically so investors prefer to focus on great people instead of great projects and invest in them with more confidence.

Selling yourself is more important than selling the idea and being a team player is one of the chief qualities in the business world. If external funding is vital to your survival then build a solid team before you go into your first meeting with the VCs.

PRO: Expanding and shrinking your team on the go

The majority of single-person businesses still contract some work out as soon as their finances allow. There are a lot of time-consuming but necessary tasks that need to be done. Bookkeeping and taxes are one of the tasks that businessmen outsource early on. Contracting work out instead of hiring a permanent employee allows you to stay flexible with your budget.

CON: Freelancers are unreliable

Working with freelancers is risky in many ways. Before you find the right people you will deal with low quality work, unreliable delivery schedules, and synchronization and communication issues. Think hard about trading the stability of a permanent team for the perceived convenience of a flexible workforce.

So is it possible for a one-man army to succeed?

You can do it! A single man with a vision and the skills to build their dream product is sometimes all one needs to succeed.

Going at it alone is a viable strategy, especially in the early stages of the startup. Just always keep your goal in front of you and don’t be afraid to grow the team once the business gains traction.