Written by Lidia Vijga
Let’s get real about what it actually takes to be a successful serial entrepreneur in tech. You’ve got one business under your belt? Great. Now it’s time to leverage that experience and create an unfair advantage for your next company. In this article, I’m going to share the strategies and advice that personally helped me start multiple ventures. So, if you’re ready to scale your entrepreneurial journey and make winning inevitable, stay with me.
What Does It Mean to be a Serial Entrepreneur?
A serial entrepreneur is someone who launches and runs multiple businesses simultaneously. These “multipreneurs,” excel in adapting to market shifts and seizing new opportunities. Serial entrepreneurship isn’t just about chasing profits; it’s a mindset embraced by visionary leaders to drive ongoing innovation and growth.
In the world of tech, serial entrepreneurs consistently innovate and create value in the ecosystem, turning every business into a learning and growth opportunity.
Driven by a fixed commitment to finding solutions to problems they’ve personally encountered or observed in the market, they often see potential where others see obstacles. The mantra of most serial entrepreneurs is simple yet powerful: “There must be a better way.”
Let me share a truth that might shock you: in startups, nobody really knows what they’re doing. Think about it. The very definition of a “startup” is rooted in innovation. If you’re launching a business with a well-established model, that’s not a really new startup – it’s just a new business. In that scenario, sure, people might know what they’re doing. But in true startups? We’re all fumbling in the dark, trying to create something that’s never existed before. That’s the thrill and the challenge of it. You’re not following a roadmap; you’re creating one as you go. So if you feel like you’re making it up as you go along, and you do it on repeat, congratulations – you’re doing it right. That’s what sets real serial entrepreneurs apart from everyone else in the tech space.
Who are the Serial Entrepreneurs?
Serial entrepreneurs in the tech space are a distinct breed. Let me break it down for you based on my experience and observations.
The Adaptability Masters
Serial entrepreneurs are the ultimate chameleons. They don’t just replicate their first success; they evolve with each new venture. They take hard-earned lessons from both their wins and failures and apply them to new opportunities.
These are the entrepreneurs who thrive on change. They’re not afraid to pivot, learn new skills, or dive into unexplored markets. They’re always asking, “What’s next?” and “How can I do this even better?”.
I’ve seen founders completely pivot their business models based on market feedback, or jump into entirely new industries armed with nothing but their previous experiences and a willingness to learn. They’re not afraid to admit when something isn’t working and change course accordingly.
Long-term Visionaries
Another thing that sets these entrepreneurs apart from most business owners is their ability to play the long game. They’re not looking for quick wins or overnight success. They understand that building something truly remarkable takes time – often a few years, not months.
While everyone else is scrambling for short-term gains, these serial entrepreneurs are laying the groundwork for multiple successful business ventures over a decade or more. They’re not just building startups; they’re building their own ecosystem. An ecosystem that often consists of multiple companies working synergistically to expedite innovation and growth. I will share more on this later.
The Wave Riders
I hear a lot of founders saying: “I just got lucky”. And this statement drives me crazy. Here’s the thing: these entrepreneurs aren’t just getting lucky. They’ve developed a sixth sense for spotting emerging trends and technologies before they hit the mainstream. It’s like they’re playing a different game altogether. While everyone else is still figuring out the rules, they’re already three moves ahead.
But then again it’s not just about “getting lucky” and spotting trends. It’s about having the guts to act on them. You’ve got to be willing to make bold moves based on your insights, even when others think you’re crazy. Remember, if everyone agrees with your idea, you’re probably too late.
Key Characteristics of Successful Serial Entrepreneurs
Now let’s get into what sets successful serial entrepreneurs apart in the tech space. If you’re already a one time founder looking to expand your portfolio, you need to grasp the core traits that these serial entrepreneurs possess.
Serial Entrepreneurs Have Fixed Vision but Flexible in Execution
I’ve learned that successful serial entrepreneurs are relentlessly stubborn about their big vision. They don’t compromise on their end goal. But what’s crucial – they’re incredibly flexible on how to get there.
This approach allows you to pivot when needed without losing sight of your ultimate objective. You might start with one business idea, realize it’s not working, and completely shift your product or business model. But your overarching vision – maybe it’s disrupting an industry in a certain way or solving a specific problem in a specific niche – remains constant.
Many Serial Entrepreneurs Can Connect Invisible Dots
Another crucial characteristic is the ability to see connections where others don’t. It’s not about having more information than everyone else. It’s about processing that information differently. As a serial entrepreneur, you need to develop this skill of pattern recognition across various industries and technologies.
This skill often leads to solutions that no one has thought before and unique business opportunities. You might notice a trend in one industry and apply it to another, or combine two seemingly unrelated ideas to create something groundbreaking. It’s this kind of thinking that gives birth to disruptive businesses and unique ideas that will help you stay ahead.
Most Serial Entrepreneurs Have Endless Curiosity
Never underestimate the power of curiosity. The most successful serial entrepreneurs I know are constantly learning, asking questions, and exploring new ideas. They often say they don’t know enough, acknowledging that there’s always more to learn. This mindset drives them to continually expand their knowledge base and seek out new perspectives.
Never ending curiosity also drives you to dig deeper, challenge assumptions, and find solutions that others might miss. Plus, it keeps you excited and engaged across multiple ventures, which is crucial when you’re running several companies at once.
Serial Entrepreneurs Got Resilience and Grit
Most founders don’t talk about it, we often just highlight big wins on LinkedIn while keeping the hardships to ourselves. In reality, we have days when we wake up feeling terrible and days where we even questioning our beliefs. What sets successful founders apart is their ability to stay determined and push forward despite these feelings. True success comes from separating your emotions from your actions and continuing to make progress, thriving even when facing adversity.
A lot of founders will agree with me – determination, resilience and grit are non-negotiable traits for successful serial entrepreneurs in tech. You must have that mental toughness and in most of times a bootstrap mentality to keep pushing forward when everything seems to be falling apart.
The Path to Success for Serial Entrepreneurs
As we already know, the success in the tech world isn’t solely about innovative ideas; it’s about timing, efficient execution, a well defined positioning, and creating a distinctive edge in a competitive landscape. Drawing from personal experience, I’ll share the key steps that guided me in identifying and pursuing my next company.
Identify Opportunities Based on Personal Experiences
When I look for market opportunities, I’m not just following trends. I’m looking for problems that I’ve personally experienced or observed. Remember, the best startups often come from solving a problem you’ve faced yourself.
While managing my second company DeckLinks, I faced a big challenge with our in-house content marketing initiatives. I was spending a huge amount of time and resources creating SEO-optimized, long-form articles for our blog. Realizing this was a common issue for many entrepreneurs, I saw an opportunity to develop a writing tool specifically for founders who handle content themselves.
Don’t be afraid to niche down. In fact, I encourage it. The more specific your target market, the easier it is to create a solution that truly resonates. You’re not trying to please everyone; you’re aiming to be indispensable to a select group. This approach allows you to build a loyal customer base that can fuel your growth. Then you expand from there.
Validate Your Idea with Paying Clients
Talk to potential customers. Build prototypes. Your first MVP could be an interactive Figma that you can share with real clients. The point here is to get real feedback before building a product. I always aim to validate my ideas through a working process and paying clients before going all in.
Remember, your goal isn’t to prove your idea is great. It’s to find out if it actually solves a problem people are willing to pay for. Be prepared to pivot based on what you learn. Some of my best business ideas came from completely changing direction after initial market validation.
Leverage Established Connections
If you are a tech founder with one company under your belt, you’ve already built valuable connections. Now is the time to activate those relationships for your next venture. Don’t hesitate to reach out to former colleagues, investors, or even competitors.
I’ve found that partnerships from my first company became the foundation for my next. For example, a customer from our initial software company BriefBid became one of our first key partners at DeckLinks, our second business.
These connections are invaluable in the startup ecosystem and can provide the support and opportunities you need to succeed again.
Learn from Previous Ventures
You’ve been through the startup journey before, and that’s a huge advantage. Every mistake, every success, every late night – it’s all valuable data for your next venture.
Here’s what I’ve learned: It’s essential to conduct a thorough assessment of your previous experiences. Analyze them. Ask yourself, “What worked? What didn’t? Why?” Maybe your marketing strategy was spot-on, but your pricing model needed work. Or perhaps your product was solid, but your distribution lagged. Identify your strengths and weaknesses, and use them to shape your new business venture.
Remember, when building startups, speed is everything. Your past experience is like a cheat code (seriously!) – it helps you move faster, avoid pitfalls, and make better decisions. Use it to your advantage. Don’t be afraid to completely change your approach based on what you’ve learned. If something didn’t work before, have the courage to try something radically different this time around.
Play the Long Game
Don’t just plan for the short term. Think about where you want your next business to be in 5, 10, or even 20 years. There’s less competition when you compete on a long-term horizon, giving you room for big, obvious moves that others might overlook.
How to navigating challenges and Setbacks in Serial Entrepreneurship
This might sound paradoxical, but the challenges you face are actually valuable assets in your entrepreneurial journey. Remember what I mentioned earlier about failing fast and learning faster? Embrace those setbacks and keep pushing forward by using every obstacle as an opportunity to grow and refine your approach.
Overcoming Common Pitfalls and Obstacles
In the startup life, as Sam Altman mentioned earlier in the video, the pitfalls are everywhere. But as a second-time founder, you’ve got an edge. You’ve already faced many of these challenges before. Remember when your first venture hit a cash flow crisis? Or when your MVP didn’t resonate with users? These aren’t failures – they’re invaluable lessons.
One common pitfall is trying to replicate your first company success exactly. Don’t fall for this trap. Each venture is unique. Instead, apply the principles that worked, but be ready to adapt your approach. Another mistake? Neglecting your network. Your connections from your first venture are gold (I know I already mentioned this). Leverage them, but don’t exploit them.
Adapting to Changing Market Conditions and Technologies
The tech world moves at lightning speed. What was cutting-edge yesterday might be obsolete tomorrow. As a serial entrepreneur, you need to be a master of adaptation. It’s not about predicting the future – it’s about being agile enough to pivot when necessary.
I’ve seen founders cling to outdated technologies because they’re comfortable with them. Don’t be that person. Stay curious. Experiment with new tools. Attend tech conferences. Read voraciously. Your ability to adapt quickly to new market conditions and technologies will give you a massive advantage in your entrepreneurial ventures.
Knowing When to Pivot, Persist, or Move On to the Next Venture
Here’s my rule of thumb: If you’re not seeing traction after giving it your all, don’t be afraid to pivot. But remember, pivoting isn’t failure – it’s a strategic move. On the flip side, if you’re seeing promising results, even if they’re small, it might be time to persist and double down. And sometimes, you need to recognize when a venture has run its course. Moving on to your next company isn’t giving up – it’s leveraging your experience for your next big win.
How to Achieve Long-Term Success as a Serial Entrepreneur
The key to long-term success lies in establishing an interconnected network of innovative companies. This isn’t just about diversification; it’s about building an ecosystem where each business venture fuels the growth of the others.
I’ve seen too many founders get stuck in a single-company mindset. But here’s the thing: when you’re running multiple companies that complement each other, you’re not just adding – you’re multiplying your potential for success across multiple businesses.
For example, one of your companies might develop an innovative machine learning model. Instead of keeping it siloed, you can implement it across your other ventures. Suddenly, every single business that in your portfolio has a competitive edge. It’s about creating a synergistic ecosystem where innovation in one area accelerates growth across your entire portfolio.
This approach not only expedites innovation but also creates a more resilient business model that can weather market fluctuations.
Furthermore, you can cross-sell services between your ventures, maximizing customer value and boosting profits across the board.
Serial Entrepreneur Examples
Let’s look at some top serial entrepreneurs. These founders have repeatedly built and scaled thriving businesses, and they show no signs of slowing down.
Elon Musk: Disrupting Multiple Industries
Elon Musk is the epitome of a serial entrepreneur who’s not afraid to think big. He’s not playing small games; he’s redesigning the board entirely. From PayPal to Tesla to SpaceX and The Boring Company, Elon Musk has a knack for identifying industries ripe for disruption and going all in.
What sets Musk apart is his willingness to take on seemingly impossible challenges. He doesn’t just start businesses; he starts businesses that aim to revolutionize entire industries. This approach embodies the idea of “rigging the game” so you can’t lose.
Oprah Winfrey: Leveraging Personal Brand
Oprah Winfrey’s entrepreneurial journey is a perfect example of leveraging personal brand to create multiple successful ventures. Starting as a talk show host, she built an empire that includes a television network, a production company, and a media conglomerate.
Oprah’s success comes from her ability to connect with her audience and transform that connection into a powerful force for business growth and social impact. Her intuitive grasp of what resonates with people has allowed her to create content and products that deeply engage and inspire her target market.
Oprah doesn’t just start businesses; she creates movements. By aligning her ventures with her values and her audience’s interests, she ensures a built-in market for each new business. It’s a powerful lesson in the value of authenticity and consistent branding in entrepreneurship.
Richard Branson: Building a Diverse Portfolio of Businesses
Richard Branson’s entrepreneurial journey is a masterclass in diversification and brand building. From Virgin Records to Virgin Atlantic to Virgin Galactic, Richard Branson has shown a remarkable ability to enter diverse markets and succeed. His approach is less about technical expertise and more about understanding consumer needs and market gaps.
Branson’s success lies in his ability to build strong teams and delegate effectively. He doesn’t try to be the expert in every field. Instead, he focuses on creating a strong brand and culture, then brings in the right people to execute the vision. This strategy allows him to operate in multiple industries simultaneously, maximizing his entrepreneurial impact.
