Thrills & Perils of a Company of One

The Future Does Not Fit in the Containers of the Past. Edition 206.

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This is the fourth in a six part series on the importance of having a “Company of One” mindset.

The first three posts covered:

1. Adopting a Company of One Mindset

2. 3 Keys for a Company of One Mindset.

3. Future Proofing Careers with a Company of One Mindset.

These posts clearly note that one does not have to be be a company of one but rather to have the mindset to thrive even in a company of thousands.

This post shares some key learnings if and when someone decides to go solo or create a side-hustle or side-gig.

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It has never been easier to launch a company of one.

67 percent of Gen-Z who have a full time job have a side gig or side hustle and within two years more people will work solo than in a company in the US.

Four factors feed this trend:

a) Unbundled and Distributed Work: The future of work for most white collar workers will be a combination of going into the office and working from anywhere with most companies eventually settling into 2 or 3 days in the office. This creates significant opportunity to pursue a second career.

b) Marketplaces: Whether it be Shopify or Etsy or Substack or You-Tube there are deep marketplaces that can support the individual by helping one create, partner, manage and generate revenue working by oneself because it is so easy to plug and play with buyers, suppliers, partners and resources.

c) Technology: AI will benefit individuals as much if not more than companies. Companies are under the mistaken belief that they will capture most of the productivity and efficiency increases brought about by AI. If one steps out of the Boardroom the conversations are very different among those who are now leveraging these tools. While AI will definitely increase productivity at companies it will significantly benefit individuals and smaller companies.

For about 100 dollars a month most individuals can have better and more updated technology than any company because of the declining cost of AI and the rate of change of technology. Most companies tech tend to be six months to a year behind the state of art that the individual can access. And the technology individuals use tend to be twice as good given the leapfrog in capabilities.

For instance most companies try to select a key partner for most technology but an individual can access state of the art from Google, Microsoft, Open AI, Mistral, Anthropic, Adobe, Eleven Labs, Runway ML for less than 20 dollars a month each with no muss or fuss. We can access huge bodies of knowledge which were usually only accessible by world class consulting companies for free or close to free.

If technology is a slingshot that enables David to play at the level of Goliath, AI turbocharges the slingshot into a cross-bow.

d) Accessible and Low Cost Infrastructure: It has never been easier to create a LLC ( a limited liability company) and set up a financial structure and basic legal frameworks. In most cases an investment of $500 to $1000 and two weeks of time is all one needs to launch oneself. The same platforms a huge company uses such as Meta or Google or Amazon or Tik-Tok is available to a company of one through their self serve models.

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The downsides of being solo or small.

Running a company of one alongside your existing job has limited risks as long as one does so with integrity (not competing with ones main job ) and without losing focus ( if one does not deliver on one’s main job one could lose it) .

Deciding to focus primarily on one’s entrepreneurial vision means being exposed to five significant risks.

1. Loss of identity: Many people’s identity are intertwined with their position and the reputation of their company.

2. Loss of community: Colleagues and supplier and partners are significant part of most peoples community and these tend to diminish quickly if one is solo.

3. Loss of benefits: The single biggest benefit loss in the US is that of health care which continues to be tightly intertwined with workplace though the Affordable Care Act and other new resources has alleviated this to a degree.

4. Uncertainty of Income: Not only does one lose income from a job but also the regular frequency of funds entering ones bank account. As a company of one income is highly variable from month to month while expenses tend to be fixed.

5. No cruise control mode: When one is working in a large company one can from time to time slack off due to health or stress or other reasons but clients and other people do not see the impact of this because other people are also working on the project. When one is on one’s own if one does not ship or deliver there is no product or service to sell. One cannot hide in a crowd.

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Ways to mitigate the challenge of a Company of One.

The best way to mitigate the challenge of a Company of One is launch it while you have a full time job and/or find ways to remain connected to the company you are leaving in a part time or advisor role if possible.

This solves for loss of identity, community, some loss of benefits and income.

For most people this is not possible today but my research for my next books suggests within three to five years most companies will offer fractionalized employment (half time or more work with full health care benefits and pro-rated equity and bonuses) because of aging and declining populations, the productivity of AI and the need to cost effectively and flexibly access a range of talents.

In the meanwhile here are five ways to minimize the perils:

1. Minimize Costs: There is no reason to spend money on office space or executive assistants or people to help you send out invoices and manage cash flow. Status does not pay the bills. It creates them. Its down and dirty time. The cost of a company of one should be just one individual. Minimizing costs provide a massive amount of optionality and runway.

2. Be Easy to Buy and Try: This is not the time to be very precious about who we work with, how much we charge or what needs to be done. Avoid insisting on minimum contract sizes, cancellation fees, advanced payments or anything that causes friction. First get bought to be sampled. Then the rest happens easily if one does a great job. Solo or small teams live and die on word of mouth so getting trial and over delivering builds a sustained business.

3. Partner Aggressively: Because one is a company of one does not mean one has to work solo. Find ways to plug into larger companies but also partner with other entrepreneurs where your skills can enhance, complement or become part of their full-service offerings. It is remarkable how many people support a company of one if one reaches out.

4. Maximize Optionality: Try to have as many different revenue streams from as many different companies or different services as you can. This enables that cash flow while wavering never goes to zero and no single client or couple of clients or jobs drive your mood and end up controlling you. Being a company of one working for just one or two people is not truly empowering. Get to a place where one can walk away from any job at any time. This way one is likely to persevere because one is not cornered or dependent.

5. Create and maintain a Reputation for Excellence: When we are a company of one we do not have the great halo of a company we may be working for. People are buying us and not a firm. This requires a reputation for excellence and delivery of excellence. Importantly one also has to invest to stay at the state of the art. At least a quarter of one’s time ends up in learning and building new skills to remain relevant and supporting one’s reputation through helping others, networking and creating a marketing presence. It is no longer about just doing great work but investing in making sure that one is capable of doing great work and people know about the great work.

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The Thrills of Company of One

While there are big risks to a Company of One and it requires significant sacrifices it does lead to four amazing benefits:

1. Control over the product and service: No longer do we have to apologize for something that went wrong in our firm that was done by someone else or struggle to fix the situation. The product and service and buck stops with one person.

2. Unleashed Freedom: Once the business begins to have momentum we can decide who we work with, what work we do and when we do it. If success is freedom to spend time in ways that gives us joy this is far more possible without the drama of bosses and P&L pressures, or clients who can control us or fussy talent that sometimes require the maintenance of high priced orchids.

3. Confidence: Talent is deep everywhere but often talent is made to feel uncertain and insecure. If one succeeds on one’s own it really buttresses ones confidence. In fact often people leave a large company and start their own business and after some success return to a corporation with far more skills and confidence than ever before. Companies will increasing look for people who have shown their ability to have built and enhanced their capabilities in new ways.

4. Future Aligned: By 2026 more people will be working for themselves in many countries then for a company. Changing demographics, completely new mindsets about life/work and amazing technology will turbo-charge smaller companies and companies of one. While there will continue to be many large companies and amazing careers at them, the container of the future of a company will be smaller, faster, more agile and more plug and play.

There will fewer whales (many of them will be slimmed down) and much more plankton.

Being a company of one is not for many people for the reasons shared above but a company of one mindset is something we should all embrace especially if we are mid level or senior in a company because the job disruptions are coming for us first as new era calls for new mindsets and the value of stores of knowledge and many forms of expertise become commodified.

For many people is time to unlearn. To unleash. To unfurl our flags.

Feel the future.

Chase it.

Rishad Tobaccowala leverages forty years of global experience across dozens of industries to help leaders and companies thrive in transformative times.