Is there ever a “right time” to start a business?
At Elephants Child, we work with business owners of all ages – and being an entrepreneur is hard work, whether you’re 25 or 55. So is there ever a perfect moment to launch a business?
In our experience, the answer is no, but age does shape how you build and grow a company. Business Growth Advisor Steve Bird, who has built and sold three technology businesses, explores how different life stages influence start‑ups.
At a glance
- Younger founders are often driven by ambition, discovery and the desire to prove themselves.
- More experienced founders tend to be guided by purpose, clarity and a focus on legacy.
- A Head (logical), Heart (emotional), Hand (practical) framework can help balance energy and experience at every stage.
- Having a clear exit plan from day one provides focus, direction and long‑term value.
The Head, Heart and Hand framework
At Elephants Child, we use a simple psychological framework to explain how we help create value:
- Head – Logical, strategic decision‑making
- Heart – Passion, purpose and emotional drive
- Hand – The practical steps to make it happen
In broad terms, we see many founders in their 20s leading with the Heart, while those in their 50s lean more on the Head. The mission also evolves:
- In your 20s, the mission is about becoming someone – the climb, the challenge, the adventure.
- In your 50s, it’s more about legacy – building a culture, shaping an industry, or leaving something that outlives the founder.
Whatever your age, our advice is the same: create a plan and define your exit from the start. When Steve launched his last business in his 40s, he decided on a trade sale from day one. That goal shaped every decision – and the business is still thriving today, long after he sold it in his 50s.
How age shapes entrepreneurship: seven key areas
1. Vision
-
20‑year‑old founder:
The mission is fluid and exploratory. They’re searching for their market, model and edge – and often themselves. The excitement lies in the unknown: “Let’s break something and see what happens.” This is the Heart ruling the Head. -
50‑year‑old founder:
The mission is more distilled. They’ve seen what works and what doesn’t. Excitement comes from clarity and solving a specific problem they’ve observed for years: “I’ve seen this gap for 20 years – now I’m fixing it.” This is the Head guiding the Heart.
In reality, both age groups use Head and Heart – the balance just shifts over time.
2. Strategy
-
20‑year‑old:
Often thinks in terms of rapid scale, market share, virality and funding rounds. With a long time horizon, they optimise for learning, exposure and opportunity. -
50‑year‑old:
Focuses on leverage, relationships, capital, expertise and reputation. They compress time by using experience and networks to skip steps. Their scalable businesses are often built around a clearly defined niche and problem.
Both need a documented plan. In early‑stage and SME deals, having a clear, credible plan can increase valuation by 25% to 100%, depending on stage and sector.
3. Motivation
-
20‑year‑old:
Often driven by proving value to investors, peers and the wider world. Success validates identity, and they can be highly self‑critical. Chaos is common. We’ve supported a start‑up that raised £3m+ from high‑net‑worth investors to build a sustainable runway, and then helped secure a Series A to extend that runway into profitability. -
50‑year‑old:
Motivated by expressing value – turning decades of skill and insight into something meaningful. Success confirms purpose. We’re currently supporting a major “buy and build” strategy with VC/trade backing, targeting £100m+ of value.
At 20, the goal is often to arrive.
At 50, the goal is to make a difference.
At 50, the goal is to make a difference.
4. Risk appetite
-
20‑year‑old:
More willing to “burn down the old system”. With fewer dependants and obligations, they can tolerate higher risk and bigger swings. -
50‑year‑old:
Still bold, but more risk‑aware. They’ve seen what failure costs, so they design for resilience and build in options.
The 20‑year‑old gambles for greatness.
The 50‑year‑old invests in legacy.
The 50‑year‑old invests in legacy.
5. Learning style
-
20‑year‑old:
Consumes ideas quickly – podcasts, mentors, accelerators. High mental flexibility, but also a risk of overload and burnout. -
50‑year‑old:
Uses experience to filter ideas fast. Decades of pattern recognition help them spot what’s fluff and what’s gold.
The youthful founder learns through trial.
The experienced founder learns through context.
The experienced founder learns through context.
6. Leadership
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20‑year‑old:
Leads through energy and audacity. People follow their belief before their track record. Strong young leaders can sell a vision and listen well, even as they learn on the job.
-
50‑year‑old:
Leads through gravitas and calm. People follow their steadiness and proven judgement. In a buy‑and‑build strategy, this often looks like a highly experienced team with real pedigree and high‑calibre leadership.
Early‑stage leadership thrives on momentum.
Later‑stage leadership thrives on trust.
Later‑stage leadership thrives on trust.
7. Handling failure
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20‑year‑old:
Failure can feel personal: “I failed, therefore I am a failure.” Yet they can also move on quickly to the next big idea – and bring others with them. -
50‑year‑old:
Failure feels more diagnostic: “That didn’t work. What’s the variable?” With more life experience, they can absorb setbacks without shattering their confidence.
The difference is psychological distance: older entrepreneurs have more narrative and context to explain what happened and what to do next.
Need support with your business?
The challenges and mindset of starting a business change with age – but one constant is the importance of thinking about your exit early. What will you need from your business to retire, start your next venture, or simply have the freedom to choose what comes next?
If you’re in start‑up or scale‑up mode, whatever your age, now is the time to start that conversation.
We work in conjunction with an extensive network of external growth advisers and SME specialists, such as Elephants Child, who have been carefully selected by St. James’s Place. The services provided by these specialists are separate and distinct from the services carried out by St. James’s Place and include advice on how to grow your business and prepare it for sale and exit.
Where the opinions of third parties are offered, these may not necessarily reflect those of St. James’s Place.
For more information on how your business plans and exit strategy fit into your wider personal finances, don’t hesitate to get in touch with Berkshire Financial Planning for expert financial advice.
