The myth of being your own boss

Recent headlines across international media and in India suggest that the pandemic has pushed thousands of “employees” to realise their entrepreneurial dreams. From trudging along as “workers”, they have now taken a leap of faith and have become their own bosses. Or so they believe in the great resignation rush that Covid-19 has unleashed upon organisations. This is irrespective of the top-dollar salary offers playing out on campuses right now.

Start-ups, by virtue of definition, are about freedom from the drudgery of reporting to a boss and not having to follow office (or work-from-home) protocols. Initially yes, in the legendary garage where the Big Idea strikes, whether in the Silicon Valley or its equivalent in Bengaluru’s Koramangala. The aura around the heroes of the start-up world has added to the lure of entrepreneurship. It could be the famous napkin sketch by founder Jeff Bezos outlining the Amazon growth strategy or his habit of taking the stairs up to the 14th floor; or Google co-founder Larry Page’s popular quotes such as ‘’if you’re not doing some things that are crazy, then you’re doing the wrong things’’ or ‘’the only way you are going to have success is to have lots of failures first’’; or Apple co-founder Steve Jobs’ lines that “simple can be harder than complex…” or ‘’your time is limited, don’t waste it living someone else’s life’’, and so on.

Cut to the present and the stories on why Twitter co-founder Jack Dorsey had to step down as the chief executive officer (CEO) capture the reality of a start-up when it has ceased to be one and yet wants to retain the spirit of entrepreneurship. According to reports, it’s not just Mr Dorsey’s involvement with payment firm Square Inc, where he is the founder and CEO, that bothered investors. His style of working too had been a problem. In 2008, when he had to quit as the Twitter CEO for the first time, one of the areas of concern for the board was that he left meetings early to attend yoga classes. Sporting a flowing beard and nose ring while spending time on meditation, yoga, travel and more recently on cryptocurrency, Mr Dorsey hardly appealed to the investors, especially Elliott Management, which has a 4 per cent stake in the social media firm. Mr Dorsey himself, however, has said that he stepped down on his own and will stay on the Twitter board till his term expires in 2022.
 

Venture capital (VC) firms—the typical moneybags for start-ups —are often contrasted with the more traditional Wall Street players in how they function and carry themselves more casually than bankers in black suit and jacket. However, there are plenty of examples both in the West and in India to show how most VCs have little patience for anything that they consider inappropriate. More importantly, most investors end up being the bosses at start-ups.

Back home, Rahul Yadav, who had co-founded Housing.com along with 11 batchmates, was in the headlines more than five years ago for his face-off with investors. Following his spat with top representatives of Sequoia Capital, the Housing.com board fired Mr Yadav as the CEO through a public statement. There was no confusion about who was calling the shots.

At Flipkart, it was Tiger Global’s top executive Lee Fixel who was reportedly behind founder Sachin Bansal’s exit from the Bengaluru e-commerce firm when Walmart acquired a majority stake in it in 2018. While Mr Bansal and Mr Fixel bonded well in the initial years, things changed after some business decisions at Flipkart didn’t appeal to Tiger Global.

In several other cases, start-ups had to fold up as investors dictated terms to founders on how to run the firms and eventually pulled out. Lavish parties, management style and deep discounts offered by start-ups have been at the centre of dispute in so many internet-led companies. Netflix series StartUp, with episodes such as “Seed Money”, “Proof of Concept” and “Hostile Takeover”, offers a glimpse into the many shades of this world.

According to an analysis published in Harvard Business Review, a few years ago, every would-be entrepreneur wants to be a Bill Gates, a Phil Knight, or an Anita Roddick…. ‘’However, successful CEO-cum-founders are a very rare breed.’’ Which, in other words, would imply that it’s one thing to be a start-up founder and quite another to be one’s own boss.