Hey bootstrappers,

You might’ve heard people say you can’t escape your past. Whether true or not, your experiences – good and bad – shape you as an entrepreneur. 

Whether you’re ghosted during job interviews, scratching your head over complex systems, or drinking away the stress of a crappy job, it all leads somewhere… 

You decide where that road goes. 

Rather than take the punch, why not fight back? Use your past to help those experiencing the same pain and frustration. This week’s founders did, and the result was profitable businesses that made them and their customers happier.

Chris Roper

Managing Editor

What Do You Do When a Brutal Job Market Rejects You? Build a Six-Figure Business That Fights Back, Says Nikita

Nikita Gupta had passed seven rounds of interviews at a big tech company only to be ghosted at the final step. A sharply worded letter followed, and a career change was born.

Like many job hunters, Nikita entered the US job market full of hope and optimism. Did it matter she’d just arrived from Singapore in the middle of a pandemic? Not a jot – Nikita was patient and used her time to learn how to job hunt while counting down the days to her first interview.

But after investing months into the hiring process to no avail, Nikita realized the system was broken. She wasn’t alone in thinking so, either, and began interacting with others online who’d experienced the same issues, often women in tech. Was it time to shake things up?

“I want candidates to take rejection personally but to learn from it. Many candidates come to me and tell me, ‘I don’t know why I’m getting rejected. I did everything right.’ And they keep going in the same feedback loop. I help them figure out what is and isn’t working.”

Wins 👍

1. Sharing her frustrating experiences online. When Nikita was ready to offer career coaching, she’d already built an audience hooked into her job search journey.

2. Inviting people to an educational webinar. Nikita asked her community if anyone was interested in career training, and four hundred showed up to her first webinar.

3. Offering productized services. One of Nikita’s earliest monetization successes was charging $49 for a resume review. It was so popular that people referred their friends.

Challenges 🤔

1. Managing her time. Nikita is a full-time technical recruiter at Uber, but FAANGPath, her side gig, is growing quickly. She leans on her team when feeling overwhelmed.

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WhatsApp for Customer Support? Not If These Founders Can Help It

Gaurav Nagani and Darshan Tank want Indian companies to focus on scalable customer service instead of trying to manage thousands of customer requests via Whatsapp.

When Gaurav and Darhsan started a mobile development agency, they also built Desku, an internal support application, to help clients log queries with their team. These same clients were so impressed with the software that they also wanted to use it to manage their customers.

Most of the cofounders’ clients couldn’t afford expensive, complex solutions like Zendesk. Clients didn’t want the expense of training people to use it either. Instead, they used Whatsapp, which didn’t scale and was a nightmare to manage.

“You can’t grow your customer base in just a couple of months with WhatsApp. Desku is a knowledge base, live chat, chatbot, and help desk. You can leverage the power of all four platforms in a single dashboard and build your chatbots using our drag-and-drop builder.”

Wins 👍

1. Taking a risk on a move and investment. Gaurav dropped out of college, moved to the city, and invested his father’s $500 into starting an agency that now makes $200,000 a year.

2. Helping DTC brands with a specific problem. Since most of these companies used Whatsapp for customer service, even a basic application would be in high demand.

3. Building a SaaS product for agency customers. Gaurav and Darshan didn’t spend a cent on marketing Desku as their agency provided its first leads.

Challenges 🤔

1. Managing a SaaS product and development agency. While the agency funded Desku’s development, the cofounders have pulled back to learn how to scale the SaaS product.

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Love, Family, and Purpose: How One Founder Discovered the Surprising Advantages of Entrepreneurship

Two failed businesses and the job from hell pushed Jace Thomas to rethink his priorities, make better decisions, and provide a better life for himself and his family.

Jace almost made it in the music industry when the band he moved to LA to join split up. Forced into the rat race, he spent the next five years selling phones in a toxic work culture that included knife fights and drug dealing on the sales floor. Drinking numbed the pain but burned him out.

Sick of the status quo, Jace sobered up, met his girlfriend, and had his first child. But how would he provide for them? He researched SEO and got a job at an agency only to later realize that he could work for himself with the skills he’d learned – especially now things were calmer at home.

“I was always kind of a wantrepreneur. Then I realized there were people making thousands online and spending tons of time with their families. That’s what I wanted to do. I’m good at design and SEO but have no dev skills, so I have to connect dots and make stuff happen.”

Wins 👍

1. Applying agile principles to SEO. Jace has productized his services into defined scope, time, and outcomes, giving him more control and shorter sales cycles.

2. Building a SaaS to rival Google Analytics. Jace has built a GA visualization tool with the help of online internship programs, pivoting to a more sustainable revenue stream.

3. Using profits for good causes. Given Jace’s challenging years in the job market, he wants to build a nonprofit to help teens and adults find meaningful, rewarding work.

Challenges 🤔

1. Contracting weak writers for content. After clients complained of poor quality content, Jace added quality control and training measures and now only hires local writers.

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