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“I walk a lonely road, the only one that I have ever known..don’t know where it goes, but it’s home to me and I walk alone”.

The widely accepted perception of these lines from Green Day’s Boulevard of Broken Dreams is that it is about going through life’s upheavals alone, lost loves, and looking to the future. But after speaking to 15+ startup founders on their bootstrapping journeys, it feels like the song was written for them.

When I relayed this idea to Arati, a startup founder who bootstrapped for 10-plus years, she vehemently agrees.

“It’s rewarding to bootstrap and all that, but the payoff comes much later,” she says, asking not to be named or attributed in any way other than her first name because she says she’s a little concerned about coming across as “weak” to potential investors she might one day need to raise funds from.

“We’re supposed to behave like starting up is easy, that we have the mental resilience to go through crap over and over again like it’s nothing..I’ve had friends who’ve lost out on VCs because they deigned to be honest about their struggles,” laments Arati.

But that’s a story for another time.

Back to the topic of bootstrapping startups and what it takes to build one, Arati says, it takes enormous patience to build a business without external money.

“You have to keep building and hoping that whatever you’re doing pays off in the longer run. Also, you have to stick around long enough..,” she says.

Stick around long enough to build the company to profitability?

“For everything…the profit, customers, scaling. I’ve wanted to give up the business at least every other year since we began in 2008. It’s incredibly hard, and you have to give a lot of yourself to it, but if you manage to, I promise you it’s worth it.”

From all the discussions I’ve had with startup founders who’ve not raised any external funding till now, the common consensus seems to be that bootstrapping is definitely, certifiably harder, and a much lonelier journey for founders, compared to those who’ve raised funding — and not just because capital concerns are somewhat allayed when one has the coin at their disposal.

“I think the availability of significant external funding gives you the cushion to not only experiment with new ideas, but also gives you enough liquidity to hire the best talent and punch above your weight in the quantum of work you can take on,” says Dr Chinmaya P Chigateri, Co-founder of Healthminds Consulting, a Singapore-based startup that provides healthcare enterprise and academia high-end data analytics and healthcare content.

“I always wish I had access to funding every time I had to pass on hiring a great candidate, driven only by the reason that we could not afford to pay his or her expected remuneration. I believe that people define an organisation, and I wished I had raised capital during such scenarios,” he adds.

Dr Chinmaya and his co-founder Shubhangini Chigateri have bootstrapped Healthminds for eight years, and are expecting to end the current financial year profitably. They’re also now looking to raise a Series A that they believe will help them scale and steer their business better.

Venture capitalists today are the cheerleaders of the startup ecosystem — a stark contrast, some say, to the crop that came before them that viewed young companies and entrepreneurs as mere dollar multipliers — and missing out on their expertise and decades of industry experience is yet another vexation in the life of a bootstrapped entrepreneur.

“It was difficult to make the connections that are necessary to construct a brand, prototypes, and more, without the support of known investors. We had to develop our consumer base and discover collaborators on our own without any introductions, guidance, and funding from others,” says Alok K Singh, Founder of Travomint, a travel booking startup.

There’s an entire network of incubators, accelerators, mentorship programmes, and sandboxes that exist today to handhold startup founders when they’re still just ideating. Schools and colleges have startup germination programmes and clubs that aim to identify and support promising entrepreneurs, and then there are huge private equity players that look to get in on the action in Series F and Series G rounds.

And while some admit their lives would’ve been easier had they just done a VC round and had doors opened for them, others disagree and say they prefer having a free hand to experiment, fail, and learn from their mistakes than have someone else telling them what to do.

“I don’t like too much interference while I am handling my business. I have a clear perspective when it comes to my business. Raising funding and having more people on board will eventually hinder the business focus..it also creates room for conflicts and, eventually, delayed decision making. I am a fast decision-maker,” says Palash Agrawal, Founder and director of Vedas Exports, a home decor and accessories company that exports the works of Indian craftsmen to foreign countries.

Palash founded the company in 2014, and says he hit profitability a long time ago.

“No regrets at all,” he quips when asked whether he regrets not raising external funding and making the decision to bootstrap.

The toll bootstrapping takes

My shadow’s the only one that walks beside me; my shallow heart’s the only thing that’s beating; sometimes, I wish someone out there will find me; ‘til then, I walk alone.

Existential loneliness is a constant companion for a majority of startup founders — bootstrapped or not.

In a survey conducted by Christina Richardson, a startup and entrepreneur coach, in 2019, she found that every single person used the word ‘lonely’ to describe their experience building their business.

There’s a tendency to “yassify” the toxic, 18-hour, no shower, no food, “hustle” culture when it comes to the startup ecosystem, and the expectation is that everyone, at every level of the company, will work themselves to the bone to build the business.

Up until now, 15-minute pep talks, 45 minutes of meditation, “mindfulness rooms”, Goa offsites, and office beer parties have been wielded as stopgaps to the fast-declining mental health of founders.

But some have sought solace in bootstrapping.

“I think I am happy I didn’t raise funds because it comes with huge responsibilities like quickly expanding to churn out more, and running behind numbers,” says Geetanjali Gondhale, Chief Designer, Founder, and CEO of Moha, a designer silver jewellery venture founded in 2014.

Vikas Singhania, Co-founder of TradeSmart Online, an online discount broking platform founded in 2013, seconds that.

“Many VCs did show interest in our company on multiple occasions. However, we did not raise VC funding to avoid the pressure and other related factors that are associated with the performance when external parties are invested in the business,” he says.

Navin Rao, Co-founder of The Kaftan Company, a sustainable loungewear and kaftan clothes venture, says, work-life balance was important for him even as he was building the company, which was founded in 2011.

“We are happy we did not raise VC funding. Keeping in mind a work-life balance while managing the expected rate of growth has proven to be positive,” he quips.

But there’s a lacerating duality to that too.

Setting your own, manageable goals that gives one enough time to play after work, and not having to chase profitability in the multiples does take the pressure off.

However, there’s then the immensity of internal pressure — of having to pay off the many people that make the business possible, family and friends who’ve invested in the company, of not failing, etc.

“Belonging to a middle-class family and setting up a business was not an easy task. I did not have any financiers — all I had was my parents’ blessings and savings along with my brother’s back,” recalls Travomint’s Alok.

“There was a trepidation inside me as I was planning to sink my parent’s hard-earned money into my startup,” he adds.

The burden of not running your family into cataclysmic financial depravity is a huge one to shoulder, and the internet is rife with stories of failed startups.

“It has certainly not been easy – not only on me, but also my family – in this journey. It does impact your mental status, which is a result of the unpredictability in the future that lurks in your mind constantly,” quips Healthminds’ Dr Chinmaya.

Putting your own neck — and money — on the line also means having to single-handedly figure the way out of any mess you may land yourself in. And to do that without any “business experts” who would’ve had an answer ready to fire can be hard.

“It definitely looks rosy on the outside now, but it has taken quite a toll on my mental health, especially during the pandemic. A lot of businesses struggled through Covid-19. As for me, it was having such negative and weak thoughts and trying to figure out how to pull myself together,” says Ritu Oberoi, Founder of ForSarees, a crafted and handwoven saree startup based out of Mumbai.

“The second and partly the third wave hit us the most. It was no longer about the finances, but about taking care of our mental health.”

Ritu founded ForSarees in 2018, and turned profitable soon after she set up the venture. COVID-19, however, severely impacted not only the startup, but also the weaver community Ritu had been working with, which added to the duress the company was already under.

“After the first lockdown, we realised that if we had raised funds, we would’ve been held accountable, but simultaneously when our capital was over and it came to paying off our marketing team, artisans, and others, I wished we had some investors to back us up. It felt like we hit rock bottom and had to start all over again when the market opened a bit,” she recalls.

Arati relays her own experience of building her Gurugram-based startup using family funds.

She says there was a time when her mother needed to undergo eye surgery because her cataract was progressing quickly. But because the family had put in every little bit they had into her business, there was nothing left to spare.

Still, instead of talking about how she couldn’t see anything properly, Arati says her mother would keep asking her questions about her day at work, discussing business matters with her and advising her.

“It was like her eye surgery was not even on top of her priority list..she was more concerned if Hyderabad ke supplier ne Baroda ke manufacturer ko raw material dispatch kiya ki nahi. And all this while, I’m standing in the middle of the room, crying, and apologising to her for landing us in this soup,” she says, breaking into peals of laughter at the absurdity of the situation.

Shivam Bajaj, Founder of Avener Capital, an investment banking startup, had a similar bon mot-studded experience to share.

“Avener Capital was set up with family funds. Ironically, my first and the most difficult deal was raising capital from my own family where I had to pitch the business idea to my family with all my conviction backed by strong data points to build a team.”

“At times, when I look back, it probably could’ve been easier to raise capital from a VC.”

Happy ending? No, but close

“The payoff is worth it..all your blood, sweat, and tears..if you stick it out, it’s worth it,” says Arati, for the fourth time during our conversation.

And it’s true. Of all the 15-odd people I spoke to piece this story together, not one said they’d do it any other way.

“Bootstrapping a business is like taking care of your own child and nurturing them until they are old enough to go out in the world,” says Priyanka Save, founder of Hill Zill Wines (Fruzzante), an alcoholic beverage company that makes fruit-based wines.

There’s a lot one learns when facing an existential crisis, and, at the cost of “yassifying” the struggle, you could even venture as far as to say that adversity builds character and teaches one things they wouldn’t have been able to digest had it just been handed to them on a platter.

“It has been a difficult ride so far, we have seen multiple ups and downs, but it has taught us a lot too, like finding out solutions for a variety of problems, learning how to build things on a budget, keeping a leaner team, wearing multiple hats, and thinking from multiple perspectives,” says Tejas Rathod, Co-founder of Mobavenue Media, a media buying startup based out of Mumbai.

Mental resilience and character building are obviously lateral advantages of bootstrapping, but Rohit Warrier, Founder of WEFIRE, a fire protection equipment supplier, argues it also teaches people to take better decisions and believe in themselves.

“Keeping yourself motivated, persevering through those times is indeed a mind game. The only thing that kept me motivated was believing in myself and that there is light at the end of the tunnel. If you keep trying without giving up, you will ultimately be able to cross the line..so the simple funda is to make a decision and never look back, no matter how bad the situation is.”

He also remarks that the objective of building and bootstrapping is to challenge yourself and find the joy in things.

“If I can do it without diluting my equity, I think I am smarter than my peers who have raised funds and are now not just answerable, but may be under more stress to make the funding work.”

Ultimately, my takeaway has been that bootstrapping is one journey you cannot truly understand until you go through it, yourself. And, so far, only those brave enough to weather the storm have managed to fare.