Jeff (Startup Whisperer)

In recent years, researchers and practitioners alike have been studying the personalities of successful startup founders to understand what makes them tick. By analysing the Big Five personality traits—openness, conscientiousness, extraversion, agreeableness, and neuroticism—we can gain insights into the characteristics that contribute to a founder's success or failure. In this blog post, we will use what a quick Google search list as the best and worst rated founders and take a look at their personality traits. However, I only did a small sample set as a quick experiment. 

Best Rated Founders

The following five founders stand out as examples of those who excel in their roles:

1. Patrick Collison (Stripe)

2. David Vélez (Nubank)

3. Max Levchin (Affirm)

4. Brian Armstrong (Coinbase)

5. Stewart Butterfield (Slack)

These founders generally exhibit high levels of openness and conscientiousness, moderate to high agreeableness, moderate extraversion, and low neuroticism. These traits help them navigate the challenges of building and growing successful startups.

Worst Rated Founders

On the other hand, there are founders whose actions and decisions led to negative consequences for themselves and their companies. Some notable examples include:

1. Travis Kalanick (Uber)

2. Elizabeth Holmes (Theranos)

3. Parker Conrad (Zenefits)

4. Billy McFarland (Fyre Festival)

5. Adam Neumann (WeWork)

Founders here often display high openness and extraversion, but extremely low conscientiousness and agreeableness, along with low neuroticism. Their actions and decision-making processes contributed to the failures of their respective ventures.

Findings

Based on the analysis of these founders, several patterns emerge:

- Successful founders typically exhibit high openness and conscientiousness, moderate to high agreeableness, moderate extraversion, and low neuroticism.

- Unsuccessful founders often show high openness and extraversion, but very low conscientiousness and agreeableness, and low neuroticism.

- Sociopathic founders are characterized by very high extraversion, very low agreeableness, conscientiousness, and neuroticism, with variable openness.

- Founders with Narcissistic Personality Disorder (NPD) tend to have high extraversion, very low agreeableness, moderately low conscientiousness and neuroticism, with no clear pattern in openness.

As Rumi once said, "What you seek is seeking you." Similarly, the qualities that make great founders also attract them to entrepreneurship. 

The Analytical Pathway: A Common Ground

Our findings reveal a striking pattern: a substantial 91.1% of top venture capitalists previously held positions in analytical fields. This statistic underscores the value of an analytical mindset in the world of venture capital. Analytical roles, encompassing areas such as financial analysis, investment management, and data-driven decision-making, equip VCs with the acumen to dissect complex market trends, evaluate business models, and make calculated investment decisions. The high percentage of VCs with this background suggests that an analytical foundation is not just beneficial but perhaps essential in navigating the intricate landscape of venture investment.

Entrepreneurial Experience: Valuable but Less Common

Contrary to the popular belief that most successful VCs are former entrepreneurs, our analysis paints a different picture. Only 21.5% of the top venture capitalists were founders before stepping into their current roles. While this figure highlights the significance of entrepreneurial experience, it also clarifies that it's less common than one might expect. Having been in the founder's shoes does provide unique insights into the challenges and dynamics of starting and scaling a business. However, it appears that having a founder's background, while advantageous, is not a predominant trait among the world's leading VCs.

Diverse Roads to the Top

The journey to becoming a top VC is diverse and multifaceted. While a strong analytical background is prevalent among these successful individuals, it is by no means the only path. The world of venture capital values a variety of experiences, whether it's steering a startup through turbulent waters or navigating the complexities of financial markets. This diversity in backgrounds contributes to a richer, more versatile approach to investment strategies, benefiting both the VCs and the innovative companies they choose to back.

Conclusion: Blending Analytical Acumen with Varied Experiences

The landscape of venture capital is as varied as it is challenging. Our analysis reveals that top venture capitalists often share a common thread of analytical experience, providing them with the skills necessary to assess and manage risk effectively. However, the path to becoming a leading VC is not monolithic. Experiences as diverse as entrepreneurship, financial management, and technology development all play a role in shaping the instincts and insights of these investment leaders. As the venture capital industry continues to evolve, the blend of analytical rigor and diverse experiences will remain pivotal in identifying and nurturing the next generation of groundbreaking companies.

As venture capitalists, we see many promising business plans from talented founders. However, the stresses of starting a company can take a toll on mental health especially since Covid. Studies show over 70% of founders report some impact on their mental wellbeing[1]. While passion and vision are critical, we must also evaluate how a founder's mental health could affect their ability to lead a successful startup. 

- Look for self-awareness and maturity. Founders who are open about their mental health needs and actively manage them signal responsibility. Seek out those who prioritize self-care and have supportive personal and professional networks.  

- Scrutinize financial planning more than usual. Impulsivity or unrealistic projections may reflect impaired judgment. Look for pragmatic financial models with executive pay aligned to value creation.

- Assess the team dynamics. Diverse, complementary teams tend to be more resilient. Watch for "red flags" like frequent turnover or poor communication that may indicate unmanaged mental health issues.

- Consider market viability to another level of detail. Evaluate the business model, competitive landscape, and addressable market.

- Provide mentorship. All founders need guidance navigating startup life's ups and downs. Be available as a sounding board and connect founders to resources like coaches, therapists, and peer support groups.

With awareness and support, founders with mental health issues can channel their creativity to build sustainable, impactful companies. As investors, we have an opportunity to foster an ecosystem where mental health is openly addressed so founders can fulfill their visions. Evaluating founders holistically is key to funding resilient startups poised for long-term success.

Times are different now, investors should be more aware of what to look for and how to help founders more going forward.

Citations:

[1] https://www.pnas.org/doi/full/10.1073/pnas.2215829120

[2] https://executive.berkeley.edu/thought-leadership/blog/impacts-poor-mental-health-business

[3] https://hbr.org/1985/05/how-to-write-a-winning-business-plan

[4] https://www.nature.com/articles/s41598-023-41980-y

[5] https://www.forbes.com/sites/melissahouston/2023/05/31/the-impact-of-mental-health-on-business-owners/?sh=266080683e41

[6] https://www.crowdspring.com/blog/what-investors-want-in-a-business-plan/

[7] https://www.forbes.com/sites/annefield/2023/04/29/startup-founders-report-entrepreneurship-is-taking-a-toll-on-their-mental-health/?sh=266a8c8e2192

[8] https://www.forbes.com/sites/tracybrower/2023/02/28/mental-health-delivers-big-business-benefits-3-strategies-for-success/?sh=2667109b3c8d

[9] https://www.linkedin.com/pulse/what-do-investors-look-business-plan-mike-kovach

[10] https://finance.yahoo.com/news/72-startup-founders-report-impact-190904214.html

[11] https://www.paychex.com/articles/human-resources/workplace-mental-health-effects

[12] https://startupnation.com/start-your-business/investors-business-plan/

[13] https://www.fastcompany.com/90969820/will-your-startup-fail-personality-traits-for-success

[14] https://hbr.org/2021/10/its-a-new-era-for-mental-health-at-work

[15] https://www.indeed.com/career-advice/career-development/business-idea-evaluation

[16] https://www.sciencedaily.com/releases/2023/10/231017215925.htm

[17] https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9969895/

[18] https://www.investopedia.com/financial-edge/0412/5-essential-steps-to-evaluating-your-business-idea.aspx

[19] https://link.springer.com/article/10.1007/s11187-018-0059-8

[20] https://blog.exit-planning-institute.org/how-owning-a-business-impacts-mental-health-and-stress-levels

[21] https://www.entrepreneur.com/starting-a-business/5-things-investors-want-to-know-before-signing-a-check/234536

[22] https://grepbeat.com/2022/07/13/startup-lifes-dark-secret-founders-often-face-mental-health-challenges/

[23] https://www.putnam.com/individual/content/perspectives/8047-mental-health-is-a-business-issue-how-companies-are-supporting-their-employees

[24] https://aofund.org/resource/what-do-investors-look-for/

I recently did a quick data analysis on Southeast Asia early stage venture capital investments in different firms over the past few years. The data (from Crunchbase) shows the ratio of investments made by each firm in a recent period of hype (March 2021 to March 2022) compared to their average number of investments over the previous 2-3 years. Let's dig into the data and see what insights we can gather. 

Overall, the data shows a fair bit of variation between firms in terms of how their recent investment levels compare to their historical averages. 

A few key observations: 

• Most firms (15 out of 17) saw increases in their investment levels compared to historical averages. This indicates an overall uptick in VC activity among these firms during the hype period. However, the degree of increase varied quite a bit. 3 firms saw modest increases of 50% or less compared to their averages. There are 2 firms that saw massive increases of 200-500% above their typical investment cadences. 

• There were 2 firms that saw decreases in investments in the 25-60% range compared to historical averages. So the pullback in investing among these firms depicted strong contrarian behavior compared with the surge in activity among the highest growing firms. 

Overall, these data reflect a VC market that saw accelerated growth in 2021 but with an uneven distribution - very few firms are pulling back showing investment discipline while others are rapidly expanding investments.