18 min read

Single Player Mode: Game On for Solopreneurship

Single Player Mode

During the enforced introspection brought on by the pandemic, I found myself mulling over the inherent complexities and often daunting challenges of coordinating efforts within a team setting. Even in the most refined and well-oiled companies, the quixotic quest for perfect alignment emerges as a monumental task.

This daunting burden — to align dozens of disparate personalities into a cohesive unit that "rows hard in the same direction" — is often what sinks companies in the early years. Not the market, not the product, not the quality of the engineering. Just the people- and personality-related shit going off the rails.

It's a constant dance to ensure harmony between co-founders, synchronize the objectives of employees and owners, balance the expectations of founders and investors, and to align the vision of current investors with future ones.

What became more apparent during my time of reflection was a rising trend that had been silently asserting its presence over the years, but seemed to burst forth prominently in the 2020s - solopreneurship.

What were once dismissed as mere 'lifestyle businesses', often seen with a condescending tilt of the head, solopreneur ventures have evolved into a legitimate and thriving category. More and more people are gravitating towards this form of entrepreneurship, embracing the freedom, control, and self-reliance it offers, as opposed to the traditional path of VC-backed ventures.

Looking forward, I believe that the advent and rapid progress of artificial intelligence will further fuel this trend.

AI acts as a powerful catalyst, giving a potent boost to the cognitive velocity of a single individual. It allows for enhanced creativity, increased productivity, and heightened effectiveness, even within a one-person team.

As we harness AI's potential more efficiently, we're likely to witness the rise of solopreneurship as not just a viable alternative, but perhaps even as a preferred choice of entrepreneurship in the years to come. I am excited and optimistic about the future of solopreneurship in this ever-evolving business landscape.

As venture-scale businesses continue to flourish, exceptional teams taking the traditional team-formation path will join forces with proactive capital allocators to pioneer advancements in fields such as space exploration, biotechnology, green infrastructure, quantum computing, and artificial intelligence – especially in training AI with novel, computationally-intensive machine learning models.

Yet, there's an impending wave of disruption set to come from solopreneurs or 'indie makers' within the still-massive realm of basic SaaS software and design and development tools, both for current and future computing platforms like Vision Pro.

These solo innovators are cutting through the clutter, utilizing tools, contracted teams, and freelancers to build multi-million dollar businesses. They choose an approach that eliminates the need for coordination efforts and eschews traditional structures like significant equity splits with co-founders, investors, boards, and liquidity preferences, and on and on.

As a result, they can navigate away from the complexities associated with alignment, financing, corporate governance, and people-related issues, and can therefore concentrate their efforts on building and scaling their businesses.

The path of the killer, the path of the indie maker

The traditional archetype of a successful business person, particularly in the realm of VC-backed entrepreneurship, often conjures the image of an individual who thrives in high-stakes negotiation, excels at team management, and demonstrates charismatic leadership. They are expected to be relentless networkers and masterful pitchers, able to convince investors of the worth of their ideas.

They succeed because they wield a certain magnetic energy and forward propulsion — sometimes coupled with technical or industry expertise — but often famously beginning as neophytes in the markets they decide to conquer.

When venturing into the jungle of startup funding, you'll soon discover that venture capitalists are hunting for this very particular species of entrepreneur. They're not just looking for anyone who can create a solid business plan or execute a profitable idea. No, they're on the hunt for this far more elusive beast. They're seeking a killer.

Who is this "killer," you ask?

Imagine a relentless force of nature, single-minded and ferociously competitive. Someone who burns with the fever of expansion and growth, often to the exclusion of all else. They are the gladiators of the business arena, going head-on into the face of insurmountable odds, armed with nothing but grit and an unquenchable thirst for success.

Having broad interests, technical expertise, a well-spoken demeanor, or even a knack for navigating the subtleties of business often aren't the sought-after traits. It's not that these qualities are undesirable; they simply do not fit the mold of the "killer" prototype.

In this high-risk, high-reward game, the "killer" is the one who takes the ruthless realities of the startup world in stride, and does so with an unsettling level of comfort and thrill.

The narrative is clear: if your startup is led by a leader who's anything less than this ideal, even if everything else is perfect—the business plan is sound, the idea innovative, and the market rapidly growing—you might still find venture capital doors closing, and productive and promising conversations ending strangely and vaguely in a "pass" or a comment that the VCs "would love to see you get more traction and track your progress over time".

Why? Because the person in the driver's seat isn't bloodthirsty enough. There's no scent of the "killer."

In the realm of venture capitalism, this pattern is nothing new. It's a function of the high-stakes nature of startup investing, where losses are the norm and the rare, explosive wins need to compensate. It's a world not suited for the faint of heart, and thus the "killer" archetype is not only sought after but also celebrated and romanticized.

On the other side of the entrepreneurship spectrum, we increasingly see solopreneurs, individuals who are both the orchestra and the conductor of their ventures.

The role of a solopreneur requires an eclectic mix of skills, often pushing the individual to be a jack-of-all-trades. They may need to learn the nuances of technical development, get their hands dirty with visual design, dive into the data-driven world of marketing, negotiate sales, and handle all the administrative tasks that come with running a business.

Solopreneurs deliberately assume all roles. They opt for a hands-on approach where they get involved in every aspect of the business. While this may seem overwhelming, it offers several distinct advantages. There's no need for coordination among different team members or departments, as everything is managed by a single person. There are no abstract governance activities or complex decision-making protocols; the solopreneur is in full control of every aspect. It's a streamlined process that allows for swift action - build, ship, and market.

This approach stands in stark contrast to the playbook of the 'killer startup CEO' as popularized in the VC-backed entrepreneurship world. The startup CEO is often urged to leverage their charisma, vision, and team-building capabilities to delegate tasks and focus on being a driving force, a visionary leader who steers the company's course.

Do killer startup CEOs also do this in the first 12-24 months of their growth venture? Sure they do — but they are oriented towards eventually firing themselves from 'doing the real work', raising outside capital, and becoming a leader of people and allocator of budgets as fast as humanly possible.

Unpacking the Solopreneur Phenomenon

Pop culture and the media have long glorified the narrative of businesses being built by groups of dynamic co-founders, each bringing their unique talents to the table to create something extraordinary.

Movies like "The Social Network" and TV shows like "Halt and Catch Fire" provide compelling narratives of multiple individuals coming together, tackling challenges, and eventually giving birth to groundbreaking companies, often with the infusion of venture capital.

This portrayal has been further reinforced by the real-life stories of tech giants such as Apple, Microsoft, and Google, which started as collaborative ventures involving more than one founder.

Co-founders can be amazing. Co-founders can go on a journey together like being in a famous rock band, or a strong and fulfilling marriage.

But co-founders can also come with downsides

  1. Conflict: Co-founders may have disagreements on business strategy, company culture, hiring decisions, and more. If not managed well, these conflicts can create a toxic environment and even jeopardize the business.
  2. Diluted Ownership: In a co-founded venture, the equity and control of the company is usually split. This means that as a founder, you have less personal ownership over the business, which can limit your decision-making power.
  3. Misalignment of Goals: Co-founders may have different visions and objectives for the business. This misalignment can cause friction and hinder the company's growth and success.
  4. Dependence: With a co-founder, there is an inherent dependence on another person. If the co-founder decides to leave or is unable to continue with the business, it can significantly disrupt operations.
  5. Decision-Making Process: When there are multiple founders, decisions often need to be discussed and agreed upon by all parties, which can slow down the decision-making process.
  6. Difference in Commitment Levels: Co-founders may have different levels of commitment to the business. One founder may be willing to devote more time and resources to the business than the other, leading to potential resentment and conflict.
  7. Distribution of Roles: Clearly defining roles and responsibilities can be a challenge. Overlapping roles or lack of clarity in duties can cause inefficiency and disputes.

In the past founders might find themselves wanting to test out various technical approaches to a market, or different markets, or different marketing strategies.

Sometimes, a venture's trajectory is impacted not by personal conflicts among founders, but by shifts in the original business plan. With each pivot, the founding team's complementary skills, once a strong asset, may become misaligned with the venture's new direction. Picture a team of co-founders as differently shaped pegs — square, round, triangular. As the venture navigates the choppy waters of startup pivots, those pegs may no longer fit their corresponding holes, creating a discord that wasn't there in the beginning.

Complicating matters further is the passage of time. Eighteen months may not seem long in the grand scheme of things, but in the startup world, it's enough time for vesting schedules to kick in, and for the cap table to be populated with convertible notes. The result? A team of founders stuck in a delicate dance, unsure whether to quit, pivot, or persevere, even when their roles no longer align with their skills or the needs of the company. It's a precarious situation, a potential pitfall of the fast-paced, high-stakes startup world.

Solopreneurs don't have to worry about this shit.

As long as solopreneurs are generating sufficient income from their products or freelance work to keep the business running, they enjoy the freedom to explore new ideas and scale up existing ones. They can rise with the morning sun, inspired to grow a podcast, venture into creating a new GPT-based AI business, sell Framer themes using Tailwind, or even engage in a 24-hour hackathon.

They can do all of this without the burdensome obligation of a decade-long mission, which traditional entrepreneurship often demands as a sworn-in-blood, at least five-to-seven-year commitment. In essence, they are unchained, free to steer their business according to their inspiration and market opportunities.

Why is solopreneurship exploding now and not, say, ten years ago? This isn't the first decade the internet has been around?

Web development is way easier now

Traditional software engineering, steeped in the principles of computer science and engineering, hasn't become any less challenging over the years. At least that's a sentiment most veteran engineers would agree with. The intricate tasks of crafting efficient algorithms, architecting scalable systems, and managing data structures — the essence of software engineering — remain as complex and timeless as ever.

However, when we pivot the conversation towards web development, we see a different narrative. Over the past decade, the process of building a web app — complete with a user interface, a server, a database, and functional capabilities — has become significantly more accessible.

In the not-so-distant past, building such an application required a wide array of specialized skills. Prospective developers needed a thorough understanding of Linux servers, in-house proficiency in managing AWS loads, an intimate and arcane knowledge of CSS intricacies and hacks just to get a damn app to look good on different screen sizes, and the capability to write complex SQL queries. This is barely even scratching the surface of the hundreds of micro-skills necessary to coordinate, design, develop and release a robust and functional web app or iOS native app in 2013.

Today, the landscape is entirely different.

The modern developer ecosystem offers a suite of services that abstract much of this complexity away. These "plug and connect" services handle many of the lower-level tasks, freeing developers to focus more on the app's functionality and less on managing its underlying infrastructure.

Take iOS development. Once dominated by the cumbersome and challenging Objective-C, iOS development today largely revolves around SwiftUI and React Native — tools that are simpler, more intuitive, and far easier for developers to wield effectively.

And consumer experiences that would have taken hundreds of hours of hacking and workarounds to pioneer, in the past, are now accesible via API: the display of augmented reality on the physical world, for instance, is plug-and-play feature of Apple's iOS developer kit.

It's important to remember that not all aspects of technology and software engineering have followed this trend.

Fields like rocket engineering, genetic engineering, and advanced machine learning continue to pose significant challenges. Yet, when it comes to web and mobile development, there's no denying the transformation.

The process of creating 'stuff for the web and mobile' is now 10 to 20 times easier than it was just a decade ago. The barrier to entry has lowered, opening up these fields to a wider range of people with diverse skill sets.

E-commerce platforms make getting paid dead simple

Building on the significant shift in the complexity of web development, platforms like Shopify, Etsy, Amazon, and Lemon Squeezy have further democratized the digital landscape. These platforms, tailored to serve the needs of solopreneurs and emerging SaaS businesses, have revolutionized the process of setting up online shops, simplifying what was once a laborious, time-consuming process.

In the past, starting an online business required extensive technical skills or a sizeable budget to hire skilled developers. Now, these platforms have made it as simple as filling out a form and uploading product images. Shopify, for instance, offers a plethora of ready-to-use templates and an easy-to-use interface that enables entrepreneurs to set up an online store in a matter of hours.

Similarly, Etsy has become the go-to platform for artisans and craft enthusiasts to sell their unique creations, removing the need for individual website management and complex payment portal setups. Amazon, with its vast consumer base, allows even the smallest businesses to access a global market, a feat previously reserved for multinational corporations.

The latest entrant, Lemon Squeezy, offers a streamlined approach to selling digital products and tiered SaaS subscriptions online. It's a testament to how far we've come in making 'stuff for the web and mobile' more accessible, even for those with minimal technical expertise.

These platforms don't just handle the creation and management of an online store. They also provide robust infrastructures to manage transactions, track inventory, engage in customer relationship management, and generate insightful analytics. All of these used to be complex tasks that required a deep understanding of databases, servers, and user interfaces, but are now conveniently bundled together, abstracted away behind a user-friendly dashboard.

While certain sectors of technology development — like the creation of novel machine learning algorithms, genetic engineering, or rocket science — remain challenging and complex, the digital landscape for entrepreneurs has been unequivocally transformed. The processes are now more streamlined, and the barriers to entry have been significantly lowered. It's a dramatic change from just a decade ago, illustrating how rapidly technology evolves and adapts to cater to emerging needs.

One social media account can be an entire marketing department

In the traditional business model, especially in VC-backed enterprises, marketing often involves a large-scale, multi-faceted approach. It typically includes building robust SEO and content marketing strategies, making substantial ad purchases, and investing heavily in both direct response and brand building ads. These methods aim at reaching a broad audience and often require significant resources, both in terms of time and capital. They also necessitate expertise in diverse areas and the coordination of multiple teams or outsourced agencies.

On the other hand, solopreneurs have pioneered a leaner, more direct approach to marketing, leveraging the power of social media platforms like Twitter, Instagram, and LinkedIn. These platforms offer an incredible opportunity to connect directly with potential customers and clients. Rather than targeting a broad, somewhat impersonal audience, solopreneurs often focus on nurturing a more personal, engaged community of followers. They can sell their first million by consistently posting relevant, engaging, and entertaining content to their tens or hundreds of thousands of followers.

This approach not only cuts down on the costs associated with large ad buys and outsourced marketing efforts but also facilitates a more authentic connection with the customer base. It is a strategy built on the principles of community, engagement, and authenticity, as opposed to the more traditional tactics of mass advertising and promotion.

SaaS has handle most of the 'company functions' up to and past the first $1 million in revenue

The proliferation of Software as a Service (SaaS) tools has played a significant role in making the solopreneurial model viable and efficient. These tools have virtually abstracted away traditional corporate departments like finance, HR, accounting, and office administration, breaking down the barriers that previously made scaling a venture a daunting task.

Take finance and accounting, for example. Platforms like QuickBooks, Xero, and FreshBooks have simplified bookkeeping, tax filing, and financial management, enabling solopreneurs to keep track of their finances with ease and precision. HR functions such as employee benefits, payroll, and talent management have been streamlined by platforms like Gusto and Zenefits, even though a solopreneur may not need these unless they start hiring.

For office administration, tools like Trello, Asana, and Slack assist with task management, project tracking, and communication, reducing the need for an office administrator. Even functions like customer relationship management (CRM) have been democratized with platforms like Salesforce and Zoho CRM, allowing solopreneurs to maintain and manage their customer interactions effectively.

These SaaS tools are making it possible for solopreneurs to manage and scale their businesses single-handedly. They can do everything that a "company" can do, but without the layers of bureaucracy and the overhead costs. They make the concept of running a business more approachable and manageable, turning what used to be an insurmountable challenge into a series of manageable tasks. As a result, solopreneurship is becoming an increasingly popular choice for individuals looking to carve out their own path in the business world.

Cloud computing is cheaper and easier than ever

There's not a lot to say here that hasn't already been said a hundred ways.

The advancements in cloud technology and the democratization of software deployment have completely transformed the landscape for solopreneurs. In essence, one can now host scalable products in the cloud, utilize edge servers across the globe for optimal performance, and deploy sophisticated software-based products at a fraction of the traditional cost. And all of this can be accomplished without hiring a single back-end server engineer in-house. It's a testament to the incredible power and potential of modern technology and its role in fueling the rise of solopreneurship.

Remote sales and marketing is more accessible

The seismic shift in buying behavior towards remote transactions is changing the game for solopreneurs and small businesses. The advent of the digital era has made physical boundaries irrelevant, enabling businesses to reach customers across the globe. In parallel, customer trust in online transactions has steadily increased, making remote purchases more common than ever before.

This shift has particular significance for software products. Once upon a time, closing a significant software deal required extensive travel, face-to-face meetings, elaborate pitches, and even the minor frustrations of ironing a dress shirt in a nondescript hotel room. However, the business landscape has changed dramatically. These days, deals worth hundreds of thousands, even millions, can be closed virtually, through video calls, screen-sharing demonstrations, and digital contract signings.

This change in business transactions has turbocharged the rise of solopreneurs and small-scale software developers. They can now build, launch, and scale their applications from the comfort of their own homes, entirely through their laptops. This new approach allows them to bypass costly sales activities traditionally required to secure large contracts, reducing their burn rate and extending their runway.

In this leaner operating model, they can reach their first million in revenue without the need for extensive travel or on-site pitches. This approach is efficient and cost-effective, and it allows these entrepreneurs to compete with larger firms without the need to invest heavily in traditional sales activities.

The removal of these barriers and costs makes it possible for more people to venture into entrepreneurship, fostering a vibrant and diverse startup ecosystem. So, while significant challenges still exist in the broader tech sector, for the solopreneur working from their laptop, the business of 'making stuff for the web and mobile' has never been more accessible, or more exciting.

Online Learning Platforms

Having the right tools and opportunities at our fingertips is only half the battle. The other half is knowing how to effectively use these resources to achieve business objectives. After all, an MBA program isn't just about learning to use software systems; it provides comprehensive education and fosters a deep understanding of business, finance, marketing, and more. Isn't that level of expertise still required? Can software tools really replace this knowledge?

Well, we are now in an era where education is no longer confined within the walls of institutions. Today, the world is our classroom. Platforms like Udemy, YouTube, Khan Academy, and even Twitter provide access to a wealth of knowledge and expertise. Whether you're looking to gain an understanding of Harvard-level economics, want to develop web development skills from scratch, or are keen to acquire an MBA-level grasp on marketing, the resources are available online, often for free. All it requires is the curiosity to seek them out and the dedication to learn.

However, what about more specific queries, challenges or roadblocks that one might face in technical areas, design, accounting, or growth strategies? Here, too, the rapid advancements in artificial intelligence come to our rescue. AI agents and assistants, trained on a vast corpus of the world's knowledge, can provide extremely personalized answers to a multitude of questions. They are like our personalized oracle, ready to assist whenever we encounter roadblocks.

Challenges of Solopreneurship

When comparing solopreneurship with leading a venture capital (VC)-backed startup, it's important to acknowledge the unique challenges presented by each business model. While the idea of working as a solopreneur — free from investor pressure, maintaining total decision-making autonomy — might seem appealing, there are substantial trade-offs to consider.

Firstly, the scale of growth potential is fundamentally different between the two models. VC-backed startups, buoyed by significant capital infusion, are equipped to scale rapidly, tap into larger markets, and achieve exponential growth. Solopreneurs, in contrast, may find their growth prospects limited by the bounds of their personal capacity, and the financial constraints of bootstrapping.

You can get way, way, way richer in some small but unlikely cases playing the venture game.

Secondly, while solopreneurs may relish their autonomy, this solo journey can mean facing tough decisions without a sounding board. On the other hand, VC-backed leaders often benefit from the expertise and mentorship of their investors and a board of directors. Yes, there might be disagreements, but these different perspectives can also lead to more balanced decisions and strategic insights.

While solopreneurs can go ask for advice on Twitter, it's not the same as having top-tier professionals with millions of dollars of skin in the game.

When investors sit down with you in that board meeting with their money on the line, they are not going to give advice that is unmoored from any real stakes. They may not always give the best advice or advice that is 100% aligned with your interests, but they will at least be highly motivated toward a growth outcome.

Similarly, employees who are taking a salary cut and are motivated by the growth of their equity stake will (usually) hit higher levels of productivity then a freelancer on a monthly retainer chipping away at the monthly sprint goals at a WordPress themes solo business.

VC-backed startups often have the resources to hire top talent and build robust teams. Solopreneurs, due to their limited budgets, may find it challenging to attract and retain skilled professionals. The lack of a dedicated team can result in a heavier workload for the solopreneur, stretching them thin across various roles within the business.

Moreover, VC-backed ventures, due to their high-profile nature, can have an easier time creating strategic partnerships, gaining media attention, and attracting further investments. Solopreneurs may find themselves struggling to make their mark in the industry and get their voices heard amidst the clamor.

Lastly, while failing in a VC-backed model can be a public and high-stakes tumble, it does often come with a softer financial landing for the founders, as the risk is shared with the investors.

For all the brutal challenges that VC-backed founders face in the gladiatorial combat of hyperscaling, they are often taking a pretty decent salary, have health benefits, and  — crucially — still get paid even if the company is burning money.

Solopreneurs are not likely to draw a six-figure salary from a venture that is not earning a profit.

With solopreneurship, permanent financial losses are also borne exclusively by the entrepreneur, leading to personal financial risk.

Predictions for the future of solopreneurship

Looking ahead, here are some predictions for the future of solopreneurship:

Maybe not growing from one to many, but from one to a few

The rise of solopreneurship will likely foster a surge of "indie makers" who, once they find their footing, will eventually decide to expand into larger teams. This natural evolution will add an interesting dynamic to the entrepreneurial landscape.

'Chief of staff' or 'Executive assistant' to a solopreneur — a very, very specialized role that involves understanding design, development, marketing, sales, admin, and the personal psychology of idiosyncratic individuals — will emerge.

SaaS will serve the solopreneur

In the technology sector, AI is set to revolutionize SaaS products. We will likely witness the advent of a new generation of AI-driven, or AI-first, SaaS products. These will be designed with the lean solopreneur company audience in mind, much like the mobile-first and cloud-first philosophies that preceded them.

Some emperors will have no clothes

Interestingly, not all that glitters on Twitter's For You feed will be gold. Some prominent solopreneurs, who have built substantial Twitter followings and appeared to 'have it all', will face irrefutable financial failure. The harsh reality that they were more adept at building a Twitter presence than a sustainable business will become clear.

On a larger scale, an upcoming recession in 2024-2025 could significantly impact the solopreneur landscape. While the overall number of successful ventures will increase, and solopreneurship will undoubtedly grow through the recession, a significant portion of entrepreneurs earning less than $2k per month may succumb to the pressures and decide to fold.

New scenes, new neighborhoods, new myths

With the evolution of the remote work phenomenon, popular solopreneur destinations like Bali and Lisbon will transform into "solopreneur digital nomad" hubs. In a way, they will mirror the development of traditional business hubs like London, New York, and Singapore over the past 150 years.

Solopreneurs will adopt spatial computing way, way before corporate offices do

A new generation of no-laptop, no-monitor solopreneurs will emerge, with the Apple Vision Pro becoming their call sign. The notion of "Put on goggles, make money. Take off goggles, live life." will redefine the work-life paradigm. The concept of an office skyscraper will become obsolete as everything one needs to run a business will be conveniently located on one's face.

Open-source will hit enter a new golden age

Finally, an entire industry focused on AI automation will take shape, resulting in an explosion of GitHub and open-source repositories. These will serve as the new 'App Store' for solopreneurs. The notion of paying a monthly fee for a corporate SaaS product will be replaced by the ability to source similar tools from GitHub for free. This shift will democratize access to high-quality business tools and further fuel the solopreneurship movement.