7 Hard-Won Business Tips From a Dropout Turned Serial Entrepreneur

Thursday, November 29, 2018

By Justin Biel, trends editor at Grow Wire

In short:

  • After dropping out of college, Logan Chierotti built and sold three companies--a real estate website, a franchise business, and a reputation management firm--before his 35th birthday.
  • By learning from mentors, becoming a student of business models, and continually self-educating, Chierotti turned three separate ideas into profitable businesses.
  • Kick-start your professional or personal growth with tried-and-true tactics from Chierotti and other successful entrepreneurs.  

When Logan Chierotti dropped out of college in the middle of his sophomore year, friends and family questioned the move. At the time, Chierotti had no business experience, nor any specific ideas about what he’d do next.

Chierotti felt he had to drop out, however. His parents weren’t covering tuition, and he was looking at taking on another $50,000 in student loans with the feeling that most of what he was learning in school didn’t apply to the “real world.”

“Everyone I know was against me leaving school,” Chierotti told Grow Wire. “They all thought it was a huge mistake, and when I left, I was quite torn and worried.” 

Chierotti’s experience is not uncommon: More than half of American college and community college students drop out before getting their degrees, according to the Washington Post. Many doubt the value of education relative to its cost, the Post adds. 


Chierotti’s entrepreneurship journey: Company #1 ...  


Chierotti dropped out of the University of Colorado, Boulder. For a while afterwards, he took odd jobs, bouncing around Denver and Boulder working as a doorman in the nightlife industry. He quickly realized this path offered little upward mobility.  

He looked at the people in his life to see how they were making money. Since his mother was a real estate agent, he set out to obtain his realtor’s license. But after he passed the state exam, Chierotti faced a major setback.

“I quickly realized people didn’t really trust a 21-year-old who looked 16 to sell their house,” he said. “Immediately I knew I had to find another way to get leads.”

Like many young entrepreneurs in the early 2000s, Chierotti turned his attention to the internet in search of sales leads. With no experience in internet marketing, he spent months studying online, learning all he could about online advertising, sales funnels and web development.

“I found I enjoyed internet marketing,” said Chierotti. “To build something and see thousands of visitors start to come was fun, like playing a real-life video game.”

He eventually created a real estate website called Colorado Home Helper, which grew into a company that became one of Colorado’s largest lead-generating websites for the real estate market at the time. Through the platform, Chierotti not only sold properties but also made a significant profit selling leads to other, more seasoned realtors throughout the state. 

Chierotti launched Colorado Home Helper, through which he gathered real estate leads throughout Colorado. 


… and Company #2 ...


Then, while still working in real estate, Chierotti met a business mentor through his personal network who worked in the franchise industry. Inspired by his mentor’s advice, Chierotti sold his real estate business to a group of Colorado realtors and dove headfirst into franchising.

Using his lead-generation background, he and a partner--whom he'd grown up with in Boulder--developed a company that acted as a brokerage between aspiring business owners and companies selling franchise opportunities. For five years, Chierotti developed this franchise brokerage business. He and his partner grew the company from two employees to more than 20, learning about each stage of business growth--hiring, scaling, managing a sales force, business operations--through online research, trial and error. 

They ran the company lean, never taking outside capital, and after a year-long process with a business brokerage firm, Chierotti and his partner sold that company, too.


… and Company #3


Their next venture was an online reputation management business, InternetReputation.com. Chierotti and his partner built the company from the ground up, grew it and sold it, all in less than five years. In 2015, at the peak of the firm’s growth, Internet Reputation ranked 583 on the Inc. 5000 list of fast-growing companies, and Chierotti sold the company.

Chierotti's third company, Internet Reputation, manages how its clients appear online.

7 entrepreneurship tips from Chierotti’s journey

Today, Chierotti spends his time consulting and mentoring and writing as a business columnist on topics like entrepreneurship, marketing and personal development. 

His trajectory reflects seven “growth tips” that other successful entrepreneurs cite often. Whether you’re starting a new organization, scaling an existing one or kicking off a project, these nuggets of wisdom are worth reviewing regularly.

1. Follow your intuition.
Intuition is our internal guidance system. Don’t be afraid to follow yours, even if the path is unconventional.

2. Take risks. 
Sometimes it pays to turn from a comfortable, safe life and do something risky. Pursue ideas that challenge you. You'll often end up where you aim, so sets your sights high.

3. Study the people you want to be like. 
If you want to achieve a goal, study and learn from the people who have the career or lifestyle you aspire to. Learn how they’ve done it, and then apply that to your life.  

4. Get the skills you need. 
If you don’t have the skills to build a company, get your dream job or enter a new field, then go and acquire them through schooling, a mentor, online courses, seminars or reading.

5. Build a strong team. 
You can only grow so far on your own. An expert team is necessary to support big-time growth.

6. Grow resilience. 
There are no overnight successes; it just appears that way from the outside. A resilient spirit is a key to growing the business or career you want.

7. Stop waiting. 
Creators who continually talk but never act rarely reach their destination. Chierotti advocates doing what you’re dreaming of today.

"What are you waiting for? The longer you wait, the harder it gets,” he said. “Take some risks, and go after your dream. Life's too short to care what other people think."

We couldn’t agree more.

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