Hey bootstrappers,

People are hopelessly inefficient, aren’t we? 

We need to eat every so often, sleep eight hours a night, and sometimes an illness throws us out of commission for days. Even worse, we often fail to focus on the things that truly matter. 

Organizations created by people mirror the flaws of their makers. Despite noble intentions, they focus on visual appeal and immediate gains over usefulness and long-term rewards – that creates broken systems. 

But our saving grace is our ability to improve. Our lineup of founders this week channeled their frustration with broken systems into profitable businesses to fix them.  

Read how they silenced naysayers and showed inefficient industries better ways to operate. 

Peter Upton (filling in for Chris)

In-house Journalist

How This Secret Service Agent’s SaaS Startup Helps Police Chiefs Hold Cops Accountable to Their Communities

Secret Service Special Agent Mudassar Malik channeled his frustration with low-accountability policing into a SaaS business holding cops accountable for their actions.

Mudassar policed in the city of St. Louis from 2004 to 2017. Then he became disenchanted after seeing repeat criminals walk free and deceitful colleagues dodge disciplinary action.

Vowing to fix police accountability, he created Officer Survey letting the local community give feedback to officers. But even though he knew exactly how to market to police forces and retain them as customers, VCs snubbed him.

That didn’t stop Mudassar in the slightest. He created and scaled his platform into a profitable business that police departments and government agencies love. It attracts plenty of investor interest too.

“I knew nothing about the tech industry or anything like it. I learned everything by watching YouTube videos or listening to hundreds of hours of podcasts on marketing, business, and SaaS. I didn’t even know what the hell SaaS stood for.”

Wins 👍

1. Recognizing an industry-wide problem. Mudassar got to see policing problems intimately as an officer. This let him create an application that actually helped both police departments and civilians alike.

2. Starting small. Mudassar knew he needed to win small police stations and municipalities first before he could get the rest on board.

3. Practicing with ecommerce. Before creating a larger application, Mudassar practiced marketing on an ecommerce apparel business.

Challenges 🤔

1. Scaling despite a lack of funding. Rejected by VCs at every turn, Mudassar needed to find new clients and grow his business himself using money out of his own pocket.

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The Need for Speed: How One Founder’s Passion Led to a Hybrid Agency Obsessed With Saving Time 

Shawn O’Neill grew frustrated when his employers ignored his requests to increase website speed. He created an agency and analytics tool to help other businesses speed up their websites and get higher conversions.

Working as a developer at an ecommerce business, Shawn always worried about slow websites increasing customer bounce rates. But unless he could prove the amount of money he’d save, his employers refused to improve their websites.

Fed up, Shawn left and created his agency, SpeedSense, to fight poor web latency across the industry. To dispel the naysayers, he created a trove of data proving his business could save clients millions.

“Website performance is a skill that needs to be taught to the in-house team. It’s not solvable by simply buying another plugin. It requires a cultural shift around high performance and delivering top-tier UX.”

Wins 👍

1. Sticking to his guns. Shawn knew he was right about slow websites hurting sales – and he found more than enough data and success to back it up.

2. Pivoting to SaaS. To help clients better understand how much money SpeedSense saved them, Shawn created a SaaS analytics tool for the data part. Now it’s another source of income.

Challenges 🤔

1. Convincing clients to buy. Shawn’s services were premium. He needed to source extremely accurate data and testimonials to prove his platform’s usefulness.

2. Changing business models. SpeedSense started as an agency because it was the best way to gain client trust. Over the pandemic, SpeedSense transitioned into a SaaS as interest in online tools grew.

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Can You Turn Lobbying Into a SaaS? These Former Think Tankers Teamed Up to Find Out

Angry at the government's bent towards big business, Jason Frye and Mary Jones quit their political careers to launch a lobbying agency for small businesses and startups.

Jason and Mary shared offices at a think tank in DC where they commiserated over wealthy donors' unequal influence on legislation. They wished smaller companies and startups had better access to government help and funding.

Years later, they created Terrapin Strategy to give startups an insider connection to Washington. To succeed, they needed to introduce masses of Washington outsiders to the intricacies of governement and keep their heads up despite skepticism from Washington insiders.

“Just because you’re not a Fortune 500 company doesn’t mean you should be scared to speak up and have a say in new ideas. Wealthy people can get ahead of everyone else in line today because they have more resources and better networks.”

Wins 👍

1. The first to do it. Mary and Jason were some of the few truly-connected Washington insiders trying to make a tech product on Capitol Hill.

2. Building in public. To market their product and solicit feedback, Jason and Mary built in public on a blog. They say it’s been an incredibly liberating experience sharing what they’ve learned.

Challenges 🤔

1. Communicating value. In lobbying, cash in doesn’t always mean results out. Jason and Mary needed to communicate Terrapin's benefits to founders clearly or risk massive churn.

2. Building tech in a legacy industry. As they built technology, Jason and Mary ran their service manually (working long hours). Only now are they building the software products that will help them scale.

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