Scaling Startup Leadership
Scaling Startup Leadership
By Epic Talent Society
April 16, 2024
Reaching unicorn status is challenging, but it can be done with the right leadership, recruitment, and culture.
“Web Summit’s host city of Lisbon continues to live up to its reputation as a home of explorers and innovators. Now a modern startup hub, the city also boasts a tech scene that’s increasingly noteworthy.”
This is the flying statement on Web Summit’s site (, the largest European tech conference for startups and corporates looking to invest. The 2022 edition took place from November 1 to 4 and welcomed 71,003 attendees, 2,296 startups, 342 partners, and more than 2,000 media members. So it is undeniable that much has been done for the startup ecosystem to flourish in the capital city of the European California – Portugal.
Finally, the government has reduced the fiscal burden on stock option holders and made preliminary reforms to further stimulate the creation of unicorns, as the new City Mayor – Carlos Moedas – recently launched the “Unicorn Factory Lisboa” aimed to help start-ups scale and achieve unicorn status.
Start Up Lisbon is a key player in helping startups and scaleups grow to achieve unicorn status. We covered quite an amount of questions and read through some interesting articles before we established our bold ideas about how leadership may contribute towards the acceleration of unicorns in our country, so we will go through our questions and findings with you.
Question 1
Is “Entrepreneurial Leadership” different from other types of leadership?
Some articles say no — it’s all hype (to be elegant, as some may say it’s BS).
Some argue that there are 6 distinct entrepreneurial leadership styles:

1. Affiliate Leadership
2. Democratic Leadership
3. Visionary Leadership
4. Pacesetting Leadership
5. Coaching Leadership
6.Transformational Leadership

We say “Yes and No”. We believe that probably 80% of the tools and techniques are common to all leaders, but 20% are different because of the mission, the context, and the stakes. These make a huge difference, and thus bear different challenges and require different “jobs to be done”.
Question 2
What is the definition of “Entrepreneurial Leadership”?
Entrepreneurial Leadership is “organizing a group of people to achieve a common goal using proactive entrepreneurial behavior by optimizing risk, innovating to take advantage of opportunities, taking personal responsibility, and managing change within a dynamic environment for the benefit of [an] organization.”
Question 3
Can we assess or even teach “Entrepreneurial Leadership”?
We found at least one site – entrepreneur scan – where you can assess your entrepreneurial leadership.
The closest we came to an answer to “can it be taught?” laid within these two papers:

1 – Entrepreneurial leadership: what is it and how should it be taught?
2 – Entrepreneurial Leadership and Entrepreneurial Success: The Role of Knowledge Management Processes and Knowledge Entrepreneurship

So the answer seems to be yes, but the “how” might take some time, so dig in on the links below.
Question 4
Why do startup founders fail?
The invo blog provided the most interesting responses to this question. Here is a summary of the top 10 reasons:

1 – Got The Idea, But Don’t Understand The Business
2 – The “Better Perfect Than Done”
3 – Reluctance To Get Feedback And Criticism
4 – The “I Won’t Sell Until I Have The Product Done”
5 – Your Startup Is Burning Cash
6 – Micromanagement Tendencies
7 – You Co-founded A Company With The Wrong Guy
8 – Inability To Raise Capital
9 – Poor Marketing
10 – Failed To Pivot
Question 5
What are the typical phases start-ups go through to reach unicorn status?
While start-ups seem to go through 5 different stages, unicorns seem to go through 7. Here they are:

1 – Idea – Everything Starts From a Good/Great Idea
2 – Analyse & Pre-seed Funding
3 – Funding search / Seed stage
4 – Market entry / Series A funding
5 – Growth / Series B funding
6 – Expansion Stage
7 – Exit Phase
Question 6
Why do Unicorn CEOs succeed?
It seems that Unicorn CEOs have 12 distinctive habits:

1 – Make Decisive Decisions
2 – Take Immediate Action
3 – S.M.A.R.T Goals
4 – Productive Not Busy
5 – Live Out Of Their Comfort Zone
6 – Make Things Simple
7 – Measure & Track Their Progress
8 – Have Positive Outlook
9 – Evolve. Grow. Develop.
10 – Character. Credible. Trust
11 – Care. Communicate.
12 – Walk Their Talk
Question 7
What are the typical leadership challenges that founders go through to reach unicorn status?
According to Jobhopin, the leadership challenges in a startup are dealing with:

1 – Limited resources
2 – Defining Vision & Goals
3 – Right Business Structure & Culture
4 – Analyse, Learn and Understand Competitors
5 – (Fostering) Constant Change
6 – Leader Reinvention

But, we like to be thorough, so we also researched articles from the top strategy firms regarding the Key Success Factors that contribute to the emergence of Unicorns. Here are a few findings that won’t dispense for interested readers, but may help the hasty ones.
In a recent article by McKinsey & Co. – Scaling up: How founder CEOs and teams can go beyond aspiration to ascent – we learned that scalers are not concerned about resources; they are managing through the chaos of growth and the amount and pace of permanent change, so they need to become elastic and that depends largely on 6 Factors:

1 – Structures specially built for product as well as portfolio growth
2 – Effective ways of working
3 – Strong talent development engine
4 – Distinctive growth culture
5 – Leadership capabilities at scale
6 – Aligned CEO with the top team
Our 3 Bold Ideas:
In the face of all the excitement we felt, we’ve decided to structure a program that would include our boldest beliefs and killer ideas in order to help these brave entrepreneurs reach unicorn status.

So after a few days of white nights, here are our boldest ideas – the ones we truly believe might make a difference – which we called the “building blocks” for the program.
Bold Idea # 1
Leadership is personal, systematic & evolutionary
Although there are more and more books published on the topic of leadership, there seems to be no clarity on the definition of leadership. This is due to the fact that leadership manifests itself in a variety of forms and formats; there is no ideal archetype, but rather an infinite combination of traits that structure unique and personal traits. Most leadership programs focus on filling gaps instead of investing in leadership strengths, so that’s where we believe we should start.

Additionally, leadership is systemic, as organizations need to combine leader development (human capital) with leadership development (social capital). In 1994, Kegan said it best: “Organizations cannot choose one or the other approach, but instead a bridge must be anchored on either side of leader and leadership development for effective development to occur.”

Leadership is also evolutionary, so founders and entrepreneurial leaders need to evolve in the way they lead if they are to mature and scale. As Keith Grint points out in his book – A Very Short Introduction to Leadership – leadership is contextual and evolves over time, thus being evolutionary. Plus, the only thing people can agree upon is that without followers, there is no leadership.

We believe that leader development is personal and leadership development is personal, systemic, and evolutionary, so we have created a synergic approach to leadership and propose to start by accepting each participant’s definition of leadership alongside their personal traits & talents to start a leadership development journey that will invite participants to scale their leadership and ventures.
Bold Idea # 2
Recruiting for the future is values & learning based
Traditional, experience based recruiting is broken. In a world of continuous learning, companies are shifting towards learning agility instead of specialization. Companies are designing “values-based recruitment” strategies and understand that handling hybrid teams is critical. Some start-ups realize that recruiting elite teams (team casting) as they transition phases is also a smart but tough endeavor.

So there is no “one-size-fits-all approach” to recruiting. But, based on each startup’s specific needs and challenges, we propose to help founders and their invited team leaders design unique recruiting strategies.
Bold Idea # 3
Culture is evolutionary and needs to be lived by all
Should we design the structure and fill in the boxes, or just get the right people on the bus and then decide where we’re going? How and when do we design the culture? These and other questions have fueled thought and action over time, but eventually businesses realize that culture has three layers: 1 – Artifacts, 2 – Espoused values and most importantly 3 – Underlying beliefs (Edgar Schein).

Leaders sigh at the notion that the only sustainable culture is the client culture. The only way to define culture is by creating diverse teams to solve client problems and seeing how that plays out. Culture needs to be discovered and lived by all employees and it’s everyone’s responsibility. We propose that founders design cultural safari strategies instead of designing them with a top-down approach and trying to activate the culture by decree.

We don’t want all this knowledge and energy to go to waste, so we decided to share it in the hope that we may even find new opportunities to deliver such a great program. If you are interested in starting an Entrepreneurial Leadership Program reach out to us and help us fly at
Dragon – A ‘unicorn’ is a startup company valued at over $1 billion. But what is a ‘dragon’? A dragon is a private company valued at $12 billion or more, net of capital raised. Here are some examples you may or may not know: AirBnB, Zynga, Flipkart, Tumblr, Spacex and Stripe.

Currently there are 24 dragons, 11 of which are based in the U.S.; the others are based in China, Australia, and the Bahamas (go figure). So, having a dragon or two is what really separates the tiers
Unicorn Facts & Figures - Did you know?
1 – There are approx. 800 Unicorns worldwide
2 – The chance of a start-up becoming a unicorn is 1 to 5 Million (that’s 0,0000002%)
3 – Less than 10% of Unicorn CEO’s are their original founders
4 – 72% of entrepreneurs lack a clear knowledge of their skills (a skill is an applied ta lent)
5 – Research suggests that the survival rates of coached entrepreneurs went from 49% to 89% in five years
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