As an entrepreneur, do you want control or do you want wealth? This “rule versus riches” dilemma shows why some founders choose to build alone while others rely on cofounders to move faster and grow bigger.
This article pulls together ideas from The Founder’s Dilemmas and related research on startup teams to explain how different types of entrepreneurs—whether lone wolves or pack-driven founders—shape their companies from day one. If you’re trying to figure out which path aligns with your goals and personality, this guide breaks down the tradeoffs so you can make decisions with more clarity.
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The Rule Versus Riches Dilemma
In The Founder’s Dilemmas, Noam Wasserman explores the contention that there are two different types of entrepreneurs: maintaining control over their company versus becoming wealthy. We’ll call this tradeoff the “rule versus riches dilemma.” He notes that most entrepreneurs achieve one or the other, but rarely both, because each path requires different strategic decisions that often conflict with each other.
Wasserman writes that control-oriented founders typically pursue a lone-wolf strategy of founding a company on their own, which lets them retain unchallenged decision-making power. Wealth-driven founders, meanwhile, are more likely to run with a pack—they tap the talent and resources of cofounders and investors to get on the path to revenue quickly.
(Shortform note: Some reviewers contend that the “rule versus riches” formulation doesn’t fully capture the complexity of founders’ motivations and goals. Although Wasserman suggests founders seek either wealth or control when starting a business, this isn’t always true, particularly in science, technology, engineering, and math (STEM) fields. Rather than being driven primarily by financial benefit or personal authority, these founders often seek to advance major breakthroughs or shifts within their domains. They view their companies mainly as platforms for proving and developing new ideas, and wealth and power tend to be secondary effects of their success rather than primary drivers.)
The Path of the Lone Wolf
Wasserman writes that choosing to be a lone wolf entrepreneur comes with advantages and inherent risks. For founders seeking maximum control (rule), the lone wolf path can be particularly attractive. Without cofounders, you maintain complete decision-making authority and avoid diluting your leadership position, allowing you to remain firmly in the driver’s seat. However, this control-maximizing approach often comes at the expense of potential wealth creation. As a lone wolf, you may end up preserving autonomy at the cost of the additional resources, skills, and connections that cofounders might bring to accelerate growth and value creation.
| The Personality Traits of Successful Founders Wasserman notes that lone wolf founders are often those who strongly value control and autonomy. While this control-driven personality type may work for some founders, recent research suggests that having diverse, complementary personalities within founding teams significantly increases a startup’s probability of success. In fact, this research indicates that startups whose leaders possess a range of personality traits—which is more likely to happen with a team of cofounders—are more than twice as likely to thrive compared to those established by solo entrepreneurs. Personality diversity within founding teams can compensate for the limitations of any single personality. Successful founding teams tend to exhibit a balanced profile across what psychologists call the “Big Five” personality dimensions: Openness to experience: Your level of curiosity, creativity, and willingness to consider new approaches (rather than rigidly adhering to tradition). Conscientiousness: The strength of your organization skills, reliability, and attention to detail—traits that become increasingly important as startups scale. Extraversion: Your capacity for socializing—in the context of a startup, this takes the form of networking, pitching confidently, and engaging with various stakeholders. Agreeableness: Your willingness to cooperate and demonstrate empathy, which is necessary for sustainable leadership. Emotional stability: Your ability to handle stress well and maintain consistent emotional responses, which helps you navigate the ups and downs of entrepreneurship. |
The Risks of Going It Alone
However, Wasserman notes that going it alone as a solo founder comes with significant challenges. Perhaps most critically, solo founders face inherent knowledge gaps—areas where they lack expertise or experience that would be covered if they had partners with complementary skills.
For example, a technical founder might struggle with coming up with a marketing strategy, while a business-focused entrepreneur might need help with product development. If you’re the only decision-maker, these knowledge gaps can lead to poor choices across critical areas of the business. You might misread market signals, make suboptimal hiring decisions, or pursue flawed strategies without anyone to challenge your thinking or offer alternative perspectives.
Another challenge you face as a solo entrepreneur is that you bear the entire burden of venture failure with no cofounders to share financial responsibilities, workload, or emotional strain. The mental and emotional toll of being the only person accountable for your company’s success or failure shouldn’t be underestimated. Without cofounders to provide support during inevitable setbacks, solo founders often experience isolation precisely when they most need encouragement.
| Combatting the Loneliness of Lone Wolf Entrepreneurship Wasserman notes that solo entrepreneurship can come with a sense of isolation as founders journey through challenges without support from cofounders. However, you can mitigate this loneliness by prioritizing active strategies to build connections and remain socially engaged. Some tactics include: 1. Sharing regular meals and coffees with others—whether business colleagues, mentors, or potential new contacts—to sustain a vibrant professional network 2. Making intentional efforts to engage in community activities, volunteering, and local or alumni events, which foster meaningful community ties and shared experiences 3. Joining structured peer advisory groups, which offer confidential forums to openly discuss your entrepreneurial struggles, receive targeted feedback, and build supportive relationships with fellow business leaders |
Running With the Pack
On the flip side, writes Wasserman, founders who prioritize “riches” over “rule” often choose to be pack dogs, embracing teamwork and shared responsibilities through cofounding arrangements. Cofounding gives founders a greater chance of financial success when they lack the necessary networks, experience, or capital to lead a company alone. This approach is especially valuable in complex, regulated, and mature markets with high barriers to entry, such as the tech and science sectors. Cofounders can fill each other’s knowledge gaps and distribute tasks based on everyone’s strengths, which creates opportunities for greater specialization and efficiency—ultimately boosting the company’s bottom line.
However, as Wasserman notes, the cofounding route requires that founders sacrifice some degree of personal authority. It also introduces an entirely new set of dilemmas around equity splits, decision-making authority, and role definition—each with its own rule versus riches implications.
(Shortform note: Even if cofounding with a team seems like the best path for you, some experts caution that too large a founding team can be counterproductive. They write that the ideal number of cofounders for a startup appears to be two or three. This helps maintain efficient decision-making and clear role definition while avoiding the complexity that comes with larger founding teams. With each additional cofounder beyond three, the complexity of relationships grows exponentially. This increased complexity often leads to a diffusion of responsibility where accountability becomes unclear and decisions stall. The more founders involved, the more interpersonal dynamics need to be managed, creating the potential for conflict and discord.)
Learn More About the Different Types of Entrepreneurs
To gain a deeper understanding of the different types of entrepreneurs, check out our guide to The Founder’s Dilemmas.
