Should you become a Parallel Entrepreneur?

There are 3 types of entrepreneurship - which one is a fit for you?

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We’re all aware of the much-overused term “Serial Entrepreneur,” but have you ever heard of a “Parallel Entrepreneur”?

Instead of betting on one big idea at a time, parallel entrepreneurs build and run several products or services in parallel, creating multiple, diversified sources of income.

Last year, I made the decision to become a Parallel Entrepreneur, and have since built multiple products such as Competely, Flawless, and DreamGift.

In this post, I’ll dive into how being a Parallel Entrepreneur differs from traditional or serial entrepreneurship. I’ll share the market and technology shifts that enable everyone to become a parallel entrepreneur. Finally, I’ll provide a framework to help you decide whether you should become a Parallel Entrepreneur yourself.

Three Types of Entrepreneurs

1. The Traditional Entrepreneur

When I started my career in the late 90s, being an entrepreneur usually meant a long-term commitment to build a single company. This period was marked by entrepreneurs who invested most of their adult lives pursuing one big idea, with the goal of building a generational business. Some examples include Bill Gates, who co-founded Microsoft in 1975 and left in 2008, Carol Bartz, who led Autodesk from 1992 to 2006, and Larry Ellison, who co-founded Oracle in 1977 and is still its chairman.

2. The Serial Entrepreneur

Serial Entrepreneurs start, grow, and exit businesses (through IPO, sale, or closure) several times throughout their careers. Oftentimes, these businesses are startup companies backed by VCs and angel investors.
Some notable serial entrepreneurs include Ev Williams (Twitter, Medium), Neil Patel (Crazy Egg, KISSmetrics, NP Digital), and Dustin Moskovitz (Facebook, Asana).
In the early 2000s, the rise of the Internet and early cloud technologies significantly reduced the time and money required to launch, market, and scale products. At the same time, Hollywood and the media started glorifying startup entrepreneurs, and being an entrepreneur became a normalized, even sought-after, career choice.

3. The Parallel Entrepreneur

Most recently, we’ve seen entrepreneurs who launch and manage multiple businesses in parallel, usually bootstrapping most of these businesses without external funding.

This includes people like John Rush, Sveta Bay, Marc Lou, and Tony Dinh, who have built multiple profitable online products. I’ve created a Twitter list of Parallel Entrepreneurs that you can follow.

In recent years, building and running multiple products have become easier:

• Modern AI, no-code platforms, site builders, and boilerplates allow the launching of new products within days or weeks.

• Automation in payments, support, and marketing makes it easier to create businesses that require minimal effort and no team to run.

• Social media allows entrepreneurs to build in public, grow their brand and followership, and generate compound effects every time they launch a new product.

• Millennials and Gen Z entrepreneurs grew up in a digital, hyper-connected world and are more adept at multitasking and adapting new technologies to run multiple businesses.

The aspiration for most parallel entrepreneurs is to build a set of products or services that generate a few million dollars per year, with no or little external funding, no or few employees, while allowing them some amount of freedom. This is not only a career choice but a lifestyle choice as well.

Parallel entrepreneurship typically doesn’t align with traditional VC funding, which involves aiming to build a billion-dollar company, taking more risks to reach outsized returns, hiring large teams, and having a singular focus on growing one business for many years.

Is Parallel Entrepreneurship For You?

None of the three entrepreneurial routes - traditional, serial, or parallel - is inherently better than the others. Each is viable in today's technology and market landscape, so the choice largely depends on personal preference.

Here’s a breakdown of the pros and cons of each route, to help you choose the right one for you:

Traditional Entrepreneur

• 👍 Pros:

  • Singular focus on one problem/market for many years builds expertise and authority

  • Opportunity to build a lasting legacy and deeply influence one industry

  • Potential for substantial long-term success and generational impact

  • Ability to create a lot of momentum and leverage through external funding, larger team, advertising, and media coverage

• 👎 Cons:

  • Spending a significant part of your adult life building a single business that might not pan out

  • Massive business goals are uncertain and may take years to reach (e.g. $10M in ARR, Market Dominance, IPO)

  • Less exposure to diverse markets, technologies, and opportunities

• 👉 Choose this path if: you're deeply passionate about a single idea and are prepared to commit to it and work hard for 10+ years, even if it doesn’t pan out

Serial Entrepreneur

• 👍 Pros:

  • Opportunity to explore several ideas and industries as an entrepreneur

  • Ability to capitalize on the business experience and networks from previous ventures

  • Higher possibility of one or more life-changing liquidity events (e.g. acquisition, merger, or IPO)

• 👎 Cons:

  • Spending several years on each endeavor, many of which might not pan out

  • Each new venture brings a fresh set of risks and challenges to overcome

  • Success in one venture doesn't guarantee success in the next

• 👉 Choose this path if: you’re okay with a long-term commitment, but enjoy the thrill of starting new ventures and are okay with starting from scratch every few years

Parallel Entrepreneur

• 👍 Pros:

  • Diversification of market, technology, and product risks

  • Potential for multiple streams of income

  • Continuous learning and exposure to new markets and technologies

  • Ability to leverage and share resources between ventures

• 👎 Cons:

  • Juggling multiple businesses and prioritizing work can be challenging 

  • Risk of losing focus and making little progress

  • High potential for burnout

  • Traditional VC funding usually isn’t an option

• 👉 Choose this path if: you thrive doing different things every week or month, have strong time management skills, and look to build a lifestyle business that suits your preferences

Why Did I Choose Parallel Entrepreneurship?

Last year, I chose to become a Parallel Entrepreneur. The primary reasons I chose this path are:

• After two decades of launching online products, I’ve become fairly good at designing, building, and launching products quickly.

• At 40 years old, my time-perspective has changed. I feel that dedicating a decade of my life to building the “next big thing” is a substantial risk if it doesn’t pan out.

• In a world that becomes more uncertain than ever, I’d rather have a diversified portfolio of products, rather than betting everything on one idea, industry, or product.

• I really enjoy the zero-to-one stage of building products from the ground up.

• I'm passionate about regularly exploring new emerging markets and technologies, particularly AI, and building new products regularly allows me to do that.

What about you? Which type of entrepreneurship is a good fit for you?
I'd love to hear your thoughts - please comment below.

Until next time,
- Lior

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1. Competely: get a competitive analysis for your product or idea within minutes. No tedious research is needed.

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3. BookAuthority: find the most recommended books to expand your horizons and learn any skill.