Building a Portfolio of Small Businesses vs One Big Bet

The question everyone asks

When people find out I run eight businesses, the first reaction is usually some version of "how?" followed quickly by "why?" Why not just focus on one thing and make it really big?

It is a fair question. The conventional wisdom says you should pick one thing and go all in. And for a lot of people, that is probably the right advice. But I have found that a portfolio approach works better for me, and I think it works better for more people than realise it.

Let me explain the thinking.

The case for one big bet

I want to be honest about the other side first, because it has real merit.

Focusing on one business means:

• All your energy goes to one thing
• You can go deeper into your market
• Decision-making is simpler
• Your team has a clear mission
• Investors understand the story

Some of the biggest companies in the world were built by people who focused obsessively on one thing for decades. There is nothing wrong with that model.

But there is a risk people do not talk about enough: single point of failure.

What happens when your one thing stops working

I started Byter, my hospitality marketing agency, in 2018. By 2020, the hospitality industry had essentially shut down. If Byter was my only source of income, I would have been in serious trouble.

Instead, I had already started diversifying. Not because I was some strategic genius. Because I had seen other agency owners go through exactly this kind of shock and I wanted a safety net.

That experience crystallised my thinking. A portfolio of businesses is not just a growth strategy. It is a risk management strategy.

How the portfolio model works

The key to running multiple businesses is not working harder. It is building each one to operate without you being in the detail every day. That comes back to the systems, automation, and AI stuff I talk about constantly.

Here is how I think about the portfolio:

Cash flow businesses: Byter and the publisher network generate consistent monthly revenue. They are not going to 10x overnight, but they pay the bills and fund everything else. Think of these as your salary.

Growth businesses: The SaaS products have higher upside but less predictable revenue. Some months are great, some are quiet. That is fine because the cash flow businesses cover the baseline.

Asset businesses: Red Cardinal, the property company, builds long-term wealth. The returns are slower but they compound. Every property we add increases the portfolio value and the passive income.

Brand businesses: lewie.io, this site, does not generate direct revenue yet. But it makes every other business easier to sell because it builds trust and authority. Think of it as marketing infrastructure.

Each business serves a different purpose in the portfolio. Some generate cash. Some build assets. Some create leverage for the others.

The shared infrastructure advantage

Here is the part most people miss. When you run multiple businesses on the same tech stack, with the same processes and the same team, the marginal cost of adding a new business drops dramatically.

My eighth business was far cheaper and faster to set up than my second. Because the infrastructure was already there. The hosting, the automation workflows, the CRM setup, the reporting dashboards. All of it transfers.

A new SaaS product for me means spinning up a Next.js project on our existing Supabase instance, connecting it to our existing n8n workflows, and deploying it on Vercel. The whole setup takes a day, not months.

The honest downsides

I would be lying if I said there were no trade-offs. There are, and they are significant.

Context switching is exhausting. Moving between businesses multiple times a day requires mental energy. I have gotten better at batching, doing all Byter work on Monday morning, Red Cardinal on Monday afternoon, SaaS on Tuesday, etc. But it is still tiring.

Nothing gets 100% of your attention. Each business gets enough attention to grow, but probably not the obsessive focus that would maximise its individual potential. I have made peace with this, but it means I probably will not build a unicorn. That is okay. I am not trying to.

Complexity compounds. Eight businesses means eight sets of accounts, eight regulatory requirements, eight customer bases with different needs. Even with systems handling most of it, the complexity is real.

It is hard to explain. When someone asks what you do and the honest answer is a five-minute explanation, you lose people. The personal brand site helps with this, but it is still a challenge.

Who should consider this model

The portfolio approach works best if:

• You get bored easily and need variety (that is me)
• You are good at building systems and delegating
• You have a strong operational foundation you can replicate
• You value security and diversification over maximum growth
• You are comfortable with "good enough" across multiple things vs "perfect" in one thing

It does not work if:

• You struggle to delegate
• You need to be deeply involved in every decision
• You are chasing a massive exit or venture funding
• You do not have the systems and automation to support it

The financial reality

I will not share specific numbers, but I will share the principle. No single business in my portfolio earns enough to be life-changing on its own. But combined, they produce a level of income and security that would be very hard to replicate with a single venture.

More importantly, if any single business failed tomorrow, I would be fine. That peace of mind is worth more than the potential upside of going all in on one thing.

Starting your portfolio

If this resonates with you, do not go and start five businesses next week. Start with one. Get it profitable. Build the systems so it can run without you in the detail. Then, and only then, start thinking about number two.

The portfolio is built over years, not months. Each addition should be deliberate and should either complement your existing businesses or serve a different purpose in the overall strategy.

Patience is not exciting. But it is how this actually works.