33 Profitable Business Ideas To Start In Chicago, Illinois

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There's no better time than now to start a business in Chicago.

Self-employment and exciting new business ideas in 2020 are on the rise - all you need is a great business idea to get started.

We've put together a diverse list of 33 profitable small business ideas you can start in Chicago today.

Here they are:

1. Home goods ($10K/mo)

Nan, Wendy and Jessica started Ocochi, a home goods business. They are now doing $10,000/month.

  • Location: Chicago
  • Revenue: $10,000/ month
  • Started: 11 months ago
  • Founders: 3
  • Employees: 3

The manufacturing process was a huge learning curve for us. With the Chinese being the artisans of bamboo and mulberry silk, our supplier journey was primarily focused on China.

Over the course of three years, we vetted over 30 factories. Initially, we had assumed that our focus would be on the vetting process and product quality, but we discovered a third and equally important element – relationship building.

Ultimately, in China nothing ends with a written contract, it comes down to trust from both sides of the partnership. Even with Jess’s understanding of the Chinese culture and language, gained at university and through working in Shanghai, there were still plenty of hurdles! It’s difficult to imagine how much harder things would have been without Jess’s experience.

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Nan, Wendy and Jessica, on starting Ocochi ($10,000/month) full story ➜

2. Live events ($291K/mo)

Brian Burkhart started SquarePlanet, a Live Events business. They are now doing $291,000/month.

  • Location: Phoenix, Arizona
  • Revenue: $291,000/ month
  • Started: over 9 years ago
  • Founders: 1
  • Employees: 7

After I decided this was my purpose — to help people improve at business communications — I looked at everything. From the way people use words to the influence of language, how the emotive side of things plays into the equation, as well as the actual design and how people look at things. I uncovered it all because I knew it all mattered.

That initial creation of stuff was very thorough, and it was fueled on a tremendous amount of excitement. It felt like we were almost inventing a lightbulb — we knew we were close, it was just a matter of putting all the parts together. Deep down to our core, we felt like we were right. Not just that we were onto something — but that we were right.

Then it became a matter of going out and making our presence known in the world. In the beginning, we offered consulting and training. The consulting aspect was going to be a bit different than other places — it was going to include us executing. See, a traditional consultancy will come up with strategy, but they typically don’t execute it. Ours was both — we were going to help people figure out what they were going to say, and then build the components — the words and visuals, and teach them to stand and deliver on those things.

how-i-started-a-7-figure-business-helping-people-give-presentations

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Brian Burkhart, on starting SquarePlanet ($291,000/month) full story ➜

3. Residential real estate. ($350K/mo)

Grigory Pekarsky started Vesta Preferred Realty, a Residential real estate. business. They are now doing $350,000/month.

  • Location: Chicago
  • Revenue: $350,000/ month
  • Started: almost 11 years ago
  • Founders: 2
  • Employees: 4

The first 18 months in the business I created a competitive edge by figuring out some marketing secrets. For example the internet was really becoming a worldwide aggregate of talent around this time, 2008/2009. So I figured out how to use worldwide talent at the cheap to post advertisements consistently and become the agent that was called the most.

However, I realized my real competitive edge was that I always picked up the phone, showed up every day and just did the work. Everyone always thinks there is some secret the most successful real estate agents keep to themselves. The reality is that we just pick up the phone more often times then not and do what we have to do to get the job done.

Of course, I have built resources and tools that have helped me stay in better touch with past clients and to make my business more efficient. However in real estate its simple to know what it takes to get to the top. Work your ass off and pick up the phone when it rings.

how-i-became-a-real-estate-agent-and-started-my-own-firm

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Grigory Pekarsky, on starting Vesta Preferred Realty ($350,000/month) full story ➜

4. Apparel and printing. ($8K/mo)

Antoine Taylor started The Cause, a Apparel and printing. business. They are now doing $8,000/month.

  • Location: Sherman Oaks
  • Revenue: $8,000/ month
  • Started: over 3 years ago
  • Founders: 2
  • Employees: 3

We really didn’t have a “Design Process” at the time.

At the time I hadn’t started my streetwear line yet so none of the designs were mine but more the logos of schools or businesses that I was doing apparel for.

Our first product was design was for my university, where it all started. For the design of the sock we used our school’s nickname, “Johnnies”, in a font we thought fit well with our name. We ordered our first batch through pre-orders.

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Antoine Taylor, on starting The Cause ($8,000/month) full story ➜

5. Shirt folds ($2K/mo)

Jay Fuller started FLXCUF, a Shirt Folds business. They are now doing $2,000/month.

  • Location: Chicago
  • Revenue: $2,000/ month
  • Started: about 3 years ago
  • Founders: 1
  • Employees: 0

Fun fact: FLXCUF actually started as “Flexcuff Shirts” five years ago. Going off of the Van Heusen flex collar I previously mentioned, I thought a shirt made sense initially. After moving to Chicago from Cincinnati (literally took a leap of faith and moved to Chicago mid-Polar Vortex in February), I took a band-aid job at Trunk Club’s warehouse folding clothes and packing trunks.

I met someone working there who had the ability to cut and stitch. I told him about the idea and sketched it out. A few days later I had a pretty jank prototype (no offense to him and his ability, it’s just funny to think about) of a dress shirt off the rack with detachable elastic bands that made the cuff’s flexible.

I eventually got connected to someone who had his own private label and worked with manufacturers overseas. I learned that my “prototype” wasn’t actually a prototype. I needed to get a sample mold made AND then begin production. I ended up getting five different shirt design prototypes. From there, I launched a Kickstarter campaign to raise funds with a goal of $15K. I pulled the plug after two weeks because the funding stalled out at $2,700. Looking back, my Kickstarter totally sucked and was rushed (I’ll revisit this later on). The silver lining -- I received A TON of private messages on how good the idea was, but an accessory would be better than a shirt. So, I went back to the drawing board with a separate band design.

how-i-launched-a-2k-month-solution-that-holds-shirt-sleeves

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Jay Fuller, on starting FLXCUF ($2,000/month) full story ➜

6. Heritage leather wallets ($60K/mo)

Phil Kalas started Ashland Leather, a Heritage Leather Wallets business. They are now doing $60,000/month.

  • Location: Chicago
  • Revenue: $60,000/ month
  • Started: about 9 years ago
  • Founders: 2
  • Employees: 8

A strong brand philosophy

The biggest advice I can give to every small business or startup is to have a strong philosophy.

At Ashland, our philosophy is to make men’s leather goods out of the best material (specifically Horween leather). You will notice that the above sentence has three very narrowly defined variables 1) Masculine market 2) Leather Goods only 3) Horween Leather Only.

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Phil Kalas, on starting Ashland Leather ($60,000/month) full story ➜

7. Boots ($2K/mo)

Matthew Walters started CODDI™, a boots business. They are now doing $2,000/month.

  • Location: Chicago
  • Revenue: $2,000/ month
  • Started: about 1 year ago
  • Founders: 1
  • Employees: 1

Having designed shoes at Under Armour for 5 years, I was incredibly fortunate to know how the manufacturing process worked overseas.

Consistency is an absolute must. When people get excited about something...they put in 100 hours the first week, and then they burn out. I don’t care if you work for 5 minutes on something...if you have a dream, work on it for 5 minutes to 5 hours every single day.

I knew what to look for… but more importantly, I knew what steer clear of. I finally landed with a factory that I was recommended by a fellow footwear designer. After finalizing my design, I handed off a tech pack to the factory and within a week, I had my first prototype:

how-i-started-a-boot-brand-and-raised-61k-with-no-paid-advertising

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Matthew Walters, on starting CODDI™ ($2,000/month) full story ➜

8. Personalized poetry at events ($35K/mo)

Daniel Zaltsman and Erick Szentmiklosy started The Haiku Guys & Gals, a Personalized Poetry At Events business. They are now doing $35,000/month.

  • Location: New York, LA, SF, Boston, Washington DC, Austin
  • Revenue: $35,000/ month
  • Started: ago
  • Founders: 2
  • Employees: 2

We can’t stress enough how valuable starting on the street was for our future success. Not only did we develop a key network of future collaborators, clients, and fans, but we also perfected the way we would go to market with it. We thought lean from the get-go always taking careful note of guest responses. While our product is not digital, we approached it as though it was.

The service itself is a brief interaction, and there are only a few things to perfect. At first, we used pharmacy-grade 3x5 notecards where the ink bled through to the other side. Our outfits were initially whatever we were wearing and not fit for a cocktail party. We asked only one question: “What would you like your haiku to be about?”

Luck and necessity played a big part in the iterations. One day on our way to write haiku at a monthly dance party, we realized we didn’t have any notecards on us and stopped at a Paper Source to grab some. They have limitless options and we found a lovely cardstock that has the look and feel of a wedding invitation. People would receive their haiku, and holding it in their fingers go “ooOoohhh, this feels nice,” before even reading it. We were booked for a fashion event on the Hornblower Infinity out of Chelsea Piers and knew that we’d look like schmucks if we didn’t show up in suits.

how-we-started-a-35k-month-business-writing-personalized-poetry-at-events

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Daniel Zaltsman and Erick Szentmiklosy, on starting The Haiku Guys & Gals ($35,000/month) full story ➜

9. Professional makeup courses ($200K/mo)

Anastasia Andreani started Vizio Makeup Academy, a Professional Makeup Courses business. They are now doing $200,000/month.

  • Location: Los Angeles
  • Revenue: $200,000/ month
  • Started: over 9 years ago
  • Founders: 2
  • Employees: 10

We invested an enormous amount of time and energy in developing this concept. We didn’t have a big budget to work with, so with very little capital, a lot of hard work and persistence, we did it ourselves. We didn’t hire any employees to help us in the beginning; it was just the two of us working nonstop, all hours of the night and every weekend, tirelessly. I find myself reminiscing of the past sometimes, and I can remember having only $100 in the bank, doubting and wondering if this was really a good idea to pursue. I can honestly say there was a voice inside me literally yelling at me with the answer YES, keep moving forward. We believed in ourselves and in each other so much that we knew in our hearts we were on the right path; we knew this was going to work and grow.

So, we started building it all from the ground up. All the makeup lessons and information taught within our courses are lessons that I and our elite makeup instructors have invested our time and hearts into. I have personally taken great pride in being able to offer my trade secrets and knowledge with others. I consider myself beyond lucky that my love of makeup and skincare, after many long years of hard work, has turned into a successful business for so many others to learn and grow from.

It was not easy at the beginning since we did not have thousands of dollars to invest. We learned everything we could about this business and how it works. Once the academy was built, we decided we wanted to create and design our own cosmetic line. We did not want to give students generic makeup products; we wanted to give them something we had created. The first 2 years were spent testing and trying new products until they worked. There was no giving up on anything we did; we kept fine-tuning and making it work.

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Anastasia Andreani, on starting Vizio Makeup Academy ($200,000/month) full story ➜

10. Professional therapeutic cuddling. ($4.2K/mo)

Samantha Varnerin started Snuggle with Sam, a Professional therapeutic cuddling. business. They are now doing $4,200/month.

  • Location: Boston
  • Revenue: $4,200/ month
  • Started: almost 4 years ago
  • Founders: 1
  • Employees: 0

If my previous answers didn’t hint to it before, I like the idea of taking action quickly rather than spending too much time testing out ideas. There are definitely areas that need more calculated and planned action to be effective and profitable, but more often than not if I’m working on something new I’ll create Minimum Viable Products (MVP’s), or the cheapest, quickest way to make a product for the public.

I didn’t have to start from scratch. I had already been doing this work for over a year and generating $500/month easily from cuddling without really trying, and I was able to bring my clients with me when I left the agency. Scaling up a bit more was easy.

Before Sam’s Snuggle School, I had Snuggle Safety: Personal Protocols, a $79 course that consisted of one 45-minute video with my voiceover (which is no longer for sale but is now a bonus module in Sam’s Snuggle School). I dragged my feet over making it for nearly a year.

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Samantha Varnerin, on starting Snuggle with Sam ($4,200/month) full story ➜

11. Disruptive naming & branding services ($250K/mo)

Darpan Munjal started Squadhelp, a Disruptive Naming & Branding Services business. They are now doing $250,000/month.

  • Location: Hoffman Estates
  • Revenue: $250,000/ month
  • Started: ago
  • Founders: 1
  • Employees: 20

With Squadhelp, the most important aspect is our focus on quality vs. quantity. We have built some advanced algorithms that determine the overall quality score of all creatives. These algorithms ensure that the creatives who consistently receive high ratings on their submissions can submit a lot more ideas in future contests. On the other hand, those creatives who do not submit thoughtful suggestions are limited in how many names they can submit in future contests.

As a result, all our contests receive a significantly high proportion of good quality, thoughtful and well-researched suggestions. This is one of the primary reasons for the significantly positive feedback we receive from our customers. We have also invested in a lot of “Gamification” features that make our platform extremely fun and collaborative.

Creatives not only receive monetary awards for winning contests, but they also receive badges and points for submitting good quality ideas. They also get featured in our monthly leaderboard, which is a coveted space for our top creatives who have won the most contests.

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Darpan Munjal , on starting Squadhelp ($250,000/month) full story ➜

12. Luxury shoes ($80K/mo)

Kartik Gurmule started KASA, a luxury shoes business. They are now doing $80,000/month.

  • Location: Nagpur
  • Revenue: $80,000/ month
  • Started: over 1 year ago
  • Founders: 1
  • Employees: 0

Being a teenager and full-time student in high school, I was unable to visit the manufacturers or their fairs in person. I was lucky enough to find the manufacture through a connection I made in the previous venture.

One should never fear failures.

Beforehand, I had the designs of the products ready as I hired designers from the UK weeks before I contacted manufacturers. I sent the designs to multiple manufacturers and ordered a sample at my home in India and one to my brother studying in Chicago. It was perfect, the blake-stitch, the leather, the quality was just excellent.

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Kartik Gurmule, on starting KASA ($80,000/month) full story ➜

13. Sweat-free shirts ($20K/mo)

Jeff Schattner started Lawrence Hunt , a sweat-free shirts business. They are now doing $20,000/month.

  • Location: Detroit, MI
  • Revenue: $20,000/ month
  • Started: over 4 years ago
  • Founders: 1
  • Employees: 2

As I mentioned, above, I don’t have a background in fashion or sewing, so I first went to Craigslist to find someone that could sew a prototype together. I received a recommendation from the local community college in the area and hired my first contractor for the business. We had a number of meetings over a few month periods, going through the design and how I wanted to make it, unlike any other shirt on the market. The prototype looked awful and was nothing you would ever want to wear, but it was good enough to bring to larger manufacturers to help with our first production run.

Initial design inspiration

Through Entrepreneur Magazine, I found out about makersrow.com - website linking designers and local manufacturers. I met with a few different facilities, and eventually settled on a local facility in Lansing, MI to help with production. It took a while to get this first run of 10 shirts completed. We went through a number of iterations of the shirt design and fabrics. We used this initial run of shirts and facility for the Kickstarter campaign that was successfully funded in August 2014.

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Jeff Schattner , on starting Lawrence Hunt ($20,000/month) full story ➜

14. Tiny books. ($10K/mo)

David Dewane started Mouse Book Club, a Tiny books. business. They are now doing $10,000/month.

  • Location: Chicago
  • Revenue: $10,000/ month
  • Started: about 3 years ago
  • Founders: 4
  • Employees: 0

Within an hour of coming up with the idea, I had got off the bus, ran to my office, and made a prototype. I showed it to the guy sitting next to me and he loved it. I immediately knew it was going to be a company and that morning I made a couple of calls to key people in my network I knew I wanted as co-founders.

This all happened around Thanksgiving and I decided to test the idea by making a hundred copies of Herman Melville’s Bartleby and sent them around to people for Christmas without telling them I made them. The feedback was genuinely positive. The following spring we built a Kickstarter campaign and got our first 1,000 customers and $50,000.

Mouse Books are not complex objects to make. Like most books today, they are laid out in Adobe InDesign. One of my co-founders was a graphic designer and we’d collaborated on a book publishing project in the past, so we knew the basic conventions of laying out a book. Still, there was a ton of trial and error as we experimented with type size, paper weight, paper color, cover design, etc. We use staples to bind, which is crucial because it limits the page count and keeps the spine flexible. Anyone can make a Mouse Book if they have a laptop, printer, and stapler.

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David Dewane, on starting Mouse Book Club ($10,000/month) full story ➜

15. Ultimate travel gadget ($15K/mo)

Craig Rabin started The Airhook, a Ultimate Travel Gadget business. They are now doing $15,000/month.

  • Location: Seattle
  • Revenue: $15,000/ month
  • Started: over 5 years ago
  • Founders: 1
  • Employees: 1

For anyone trying to invest in a new product… know it’s not as easy as it was coming up with the idea and sketching it on your bar napkin. You will find good days and bad day along your journey. In the case of The Airhook, we spent 13 months developing the concept.

Design – build – break – repeat

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Craig Rabin, on starting The Airhook ($15,000/month) full story ➜

16. Sexy chairs and stylish accessories ($37K/mo)

John Humphreys started Humphreys, a sexy chairs and stylish accessories business. They are now doing $37,000/month.

  • Location: Austin
  • Revenue: $37,000/ month
  • Started: over 3 years ago
  • Founders: 1
  • Employees: 1

The first product we designed was the chair. It was slow to get started because there was a huge intimidation factor. I did the classic, “I’ll do it tomorrow” thing. I didn’t feel confident and certainly didn’t think I was capable. Although I wanted to do it, I delayed it out of fear.

A business is a linear progression that requires constant effort.

A friend approached me and told me to do it now. She invited me to stay with her and her family who had a billiard manufacturer in Ontario in a town called Goderich. This is where we set out on a novice adventure to build this chair. We had paper sketches and cheap Walmart mock-ups of the seat and that began a year and a half process that I thought would take 3 months.

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John Humphreys, on starting Humphreys ($37,000/month) full story ➜

17. Special event design and production ($333K/mo)

Natasha Miller started Entire Productions, a Special Event Design and Production business. They are now doing $333,300/month.

  • Location: San Francisco
  • Revenue: $333,300/ month
  • Started: over 19 years ago
  • Founders: 1
  • Employees: 12

Entire Productions started off sending out classical string ensembles and jazz bands out to social and corporate events.

We then added other offerings such as dance bands, DJ’s, aerial and circus artists, live-event painters, cigar rollers, headline celebrities, etc. A lot of our challenges are educating our musical and artistic talent what the expectations on a special event are which are very different than what they’re used to at bars, clubs, festivals where there aren’t many restrictions for behavior, interaction with guests and drinking, etc. I knew a lot of classical, jazz and pop/rock musicians from being a musician myself. I had to branch out of my world to engage with DJ’s and circus arts performers- I also had to learn the lingo that comes with each discipline. Asking people who they know, finding them at their public performances as well as sourcing and qualifying talent online are the main methods I used to find this talent.

Research your competitors and figure out what makes you unique, different and why your customers should really choose you. Deliver impeccable services or products. There’s no shortcut to this!

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Natasha Miller, on starting Entire Productions ($333,300/month) full story ➜

18. Music licensing clearance. ($210K/mo)

Aaron Green started Easy Song Licensing, a Music licensing clearance. business. They are now doing $210,000/month.

  • Location: Minneapolis
  • Revenue: $210,000/ month
  • Started: about 15 years ago
  • Founders: 2
  • Employees: 6

Around 2008, Mark sensed that the school and church mobile recording business would not make us billionaires, so he became quite sophisticated with mechanical song licensing laws, and had built a website to organize and maintain our licensing registration, ongoing reporting, royalty disbursement and publishing contacts. Like writing a hit song, he envisioned a new business to help the average indie artist bridge the gap between themselves and large music publishers, so we invested in the domain name “EasySongLicensing.com”.

At this time, we were knee-deep in Legacy recordings, in which I specialized in handling the sales and marketing department, and Mark did all the bookkeeping, licensing and website maintenance. We worked extremely hard and kept trying to expand further and further, just earning enough for us to keep the same salary for virtually 10 years, leaving us even more hungry, and unsatisfied with our career and business goals. Something needed to change. We needed to diversify and take the music industry knowledge we had acquired, and turn it into something special, not just status quo.

Meanwhile, in the independent song licensing world, at this time, there were basically 2 competitors; the Harry Fox Agency and Limelight. HFA is the original US licensing agency since the 1920’s connecting most major and mid-level publishers and copyright holders with the public for audio-only album releases and singles. Limelight was their main competitor at the time, and we were not even a blip off the radar. ESL was not a full-time business to start (2008), in which Mark handled this in his small pockets of time and I was still trying to expand our Legacy recording business. Then, all of a sudden, in December of 2014, our entire lives changed significantly when Limelight announced it was shutting down and leaving our industry.

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Aaron Green, on starting Easy Song Licensing ($210,000/month) full story ➜

19. Sneakers reseller ($5K/mo)

Chris Casseday started 513 Kicks, a sneakers reseller business. They are now doing $5,000/month.

  • Location: Cincinnati
  • Revenue: $5,000/ month
  • Started: about 3 years ago
  • Founders: 1
  • Employees: 1

Fortunately, with my business, I did not have to go through all of the hoops that are required when designing, prototyping, and manufacturing a new product. My business is simply taking manufactured goods (sneakers) and strategically selling them to the right people at the right prices.

You must have a passion for growing your business, whatever it might be - selling sneakers, providing services, etc. The honeymoon phase can wear off quickly and that is when some people throw in the towel.

The law of supply and demand is a huge factor in the secondary sneaker reselling market. As a result, it is crucial to know what you’re selling, and where you’re going to sell it. Sourcing inventory that will sell for a profit requires a significant amount of research before you spend a dollar on anything. In the case of sneakers, before buying a pair to resell, I check the comparable sales (if applicable) to determine the current average sale price and overall market demand. Back in the early 2000s, this was not an easy process. I relied on completed eBay sales primarily, and then actual one to one conversations that I had online with other sneaker enthusiasts.

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Chris Casseday, on starting 513 Kicks ($5,000/month) full story ➜

20. Shirts that start conversations. ($200K/mo)

TJ Mapes started RIPT Apparel, a Shirts that start conversations. business. They are now doing $200,000/month.

  • Location: Chicago
  • Revenue: $200,000/ month
  • Started: about 11 years ago
  • Founders: 3
  • Employees: 0

The next piece of this puzzle was to find a screen printer who could print all the millions of t-shirts we were about to sell (hehe). We actually lucked out because Matt’s Dad was an investor in a small screen printing company back in our hometown.

This was a huge break for us because we didn’t have to search for a printer and we ended up getting a great deal on printing. PLUS they were going to fulfill all our orders for us too.

Things didn’t stay peachy for long though as the daily nature of the business proved difficult to keep up with and also this small printer wasn’t used to printing highly artistic designs with lots of colors and detailed halftones.

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TJ Mapes, on starting RIPT Apparel ($200,000/month) full story ➜

21. Bag storage. ($15K/mo)

Cody Candee started Bounce, a Bag storage. business. They are now doing $15,000/month.

  • Location: San Francisco
  • Revenue: $15,000/ month
  • Started: over 2 years ago
  • Founders: 2
  • Employees: 1

Aleks and I were brainstorming new business ideas when I mentioned the idea of “an Uber for your things.”

We decided to put up a landing page for bag storage and delivery in New York City. We did this in 3 hours using a basic landing page builder, plugged in Adwords and had our first customer request a “Bounce” 5 minutes later. We literally hopped on Citi Bikes to fulfill our first orders, and from then on the customers kept coming.

Think to yourself: How can I start this month? This week? Today? There’s probably something you can do immediately to get started.

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Cody Candee, on starting Bounce ($15,000/month) full story ➜

22. Executive reputation growth & management ($550K/mo)

Bant Breen started Qnary, a Executive Reputation Growth & Management business. They are now doing $550,000/month.

  • Location: New York City
  • Revenue: $550,000/ month
  • Started: over 8 years ago
  • Founders: 1
  • Employees: 25

I hired a group of offshore developers to help code the initial prototype based on a blueprint that I’d mapped out. The initial MVP (minimal viable product) was extremely rough and messy. I started with grandiose plans and the developers partially executed elements of all of them but did not deliver a cohesive whole. I don’t think the MVP ever fully worked when we went to raise an additional allotment of investment needed to build out the next phase of the platform. To get around the MVP’s shortcomings I only demoed one part of the solution related to generating a rules-based engine structured scan of someone’s LinkedIn profile.

The buggy MVP led several early-stage investors to pass on the project. However, when I curtailed the platform demo in the investor presentations and showed interactive screens of the desired functionality instead we finally raised the money needed for a 1.0 version of the platform.

I used the seed funding to hire a couple of the key members of the team Mark Pilatowski and Ray Carbonell and found another offshore development group to realize the vision. Qnary 1.0 was significantly better than the MVP. While the design was a bit messy and certainly not what we ideally hoped for the rules-based optimization steps worked.

how-i-started-a-550k-month-executive-online-reputation-management-solution

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Bant Breen, on starting Qnary ($550,000/month) full story ➜

23. Editing & co-authoring services ($3K/mo)

Pat Stainke started The Language Delegate, a Editing & Co-Authoring Services business. They are now doing $3,000/month.

  • Location: Donna, Texas
  • Revenue: $3,000/ month
  • Started: over 6 years ago
  • Founders: 1
  • Employees: 1

My only product is an edited document, so my start-up costs were minimal. All I needed was a computer and access to a couple of online job boards. I did not incorporate right away, but I found that the cost of incorporating a freelance business was minimal. Bidding on jobs has been my largest ongoing expense (detailed in another section, below).

As an editor, I start with the mechanics: grammar, spelling, punctuation, verb tense, and effective word choice. Because I write in other languages, I have sharp instincts for these details. However, mastering the mechanics is not enough to guarantee a compelling piece of writing. As a wordsmith, I massage the language to have a better flow and to sound more naturally idiomatic, while preserving the author’s voice. If something is not clear, I suggest ways to improve the reader experience. When I work on academic pieces, it is often necessary to strengthen a piece’s structure. My goal is to be the silent partner who ensures that each piece is as polished as possible before they go to press.

As a co-author, I take things beyond these two steps and let my ‘inner storyteller’ run loose (all in service of the client, of course!). I dig deep into the characters, the setting, and the dialogue as I weigh the import of a particular scene or historical event. I enhance dialogue or extend short clips into lengthier passages to strengthen a point or to beckon the reader to linger in a moment that is pivotal to the unfolding narrative. I’ve been blessed to work with several authors (both fiction and non-fiction) who have trusted me to add another dimension to their pieces in this way. (I include more about co-authoring at the end.)

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Pat Stainke, on starting The Language Delegate ($3,000/month) full story ➜

24. Film, tv & media production ($5K/mo)

Latham Ford started No Idea Films, LLC, a Film, TV & Media Production business. They are now doing $5,000/month.

  • Location: Hollywood
  • Revenue: $5,000/ month
  • Started: about 3 years ago
  • Founders: 1
  • Employees: 4

My first time producing a film was actually a film I wrote and produced and starred in, which won my biggest award as a film creator to date. But that’s only the fruit. Let’s talk about the labor, and how I underestimated the work that goes into producing, from casting the actors, getting the film crew, finding extra hands, locking down a location, equipment, contracts, you name it. I don’t think I slept for 3 days. I made a lot of mistakes, ran into a few walls but I gained so much experience. It made my next production much easier… not to say it was. I don’t think any productions ever are easy.

One of my favorite things about producing is that I get to pick my family because that’s what we become in those days. Everyone is working hard to make this one idea happen. We laugh, we have fun, we eat well and work hard. It is a very gratifying thing to yell “It’s a wrap!” but then to have to leave the people you’ve been in the trenches with, sucks, but that’s the life of production. BTS LINK: Supra Footwear

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Latham Ford, on starting No Idea Films, LLC ($5,000/month) full story ➜

25. Outdoor gear. ($20K/mo)

Chez Brungraber started Gobi Gear, a Outdoor gear. business. They are now doing $20,000/month.

  • Location: Bend, Oregon
  • Revenue: $20,000/ month
  • Started: almost 6 years ago
  • Founders: 2
  • Employees: 1

Turns out… manufacturing is one of the hardest parts of running a business. Not only does inventory mean you are cash poor (or vice versa), but any delays or issues with manufacturing can drastically hurt your bottom line.

Gobi Gear started slowly, very slowly, as I was limited to a small initial investment ($20K), meaning a small quantity order to begin (3000 units). In retrospect this was good for us - it allowed us to not overextend early, and maneuvering to meet customer wishes was easy.

We found our first China factory on Alibaba, through months of research and prototype samples. We have also worked with agents, local to China and the USA, and in the end, decided it best to just work directly with the factories.

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Chez Brungraber, on starting Gobi Gear ($20,000/month) full story ➜

26. Unique instruments. ($100K/mo)

Adam Klosowiak started KLOS Guitars, a unique instruments. business. They are now doing $100,000/month.

  • Location: Provo
  • Revenue: $100,000/ month
  • Started: about 5 years ago
  • Founders: 2
  • Employees: 13

My brother and I were both broke college students when we started KLOS Guitars, and this really forced us to be extremely lean. When you have no money, you really have to get creative with how you get the things you need, be it information or materials.

The qualities that we wanted the first model of the KLOS guitar to have were pretty clear to us from initial market research. We wanted the guitar to be the most affordable carbon fiber guitar on the market so that people like ourselves (college students at the time) could afford it.

The reality is that there will always be mistakes when you’re starting a company, and in hindsight vision will always be 20/20. The best thing to do is to create a minimum viable product as fast as possible, launch it as it is, and start interacting with the market.

how-we-invented-a-carbon-fiber-guitar-and-grew-to-1m-year

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Adam Klosowiak, on starting KLOS Guitars ($100,000/month) full story ➜

27. Fun & colourful groomsmen socks ($17.8K/mo)

Mari & Matt McNamara started No Cold Feet LLC, a Fun & Colourful Groomsmen Socks business. They are now doing $17,800/month.

  • Location: Chicago, IL
  • Revenue: $17,800/ month
  • Started: over 3 years ago
  • Founders: 2
  • Employees: 0

Our product design process was relatively simple compared to other physical products or even other textiles. We began by reaching out to manufacturers on Alibaba, maybe twenty or so originally, and narrowed down to six for quoting and samples. Because socks are fairly standard sizing you essentially pick your target size (e.g. average men, children’s, etc) and then provide a design to the manufacturer who converts it to the file that a knitting machine requires.

We found a blank template for sock design online and had a graphic designer (a previous co-worker of Matt’s) create all of the patterns that would eventually become our first round of socks. The colors were chosen based on what would match with standard formal wear for weddings plus a few others that were more aligned with the seasons. We started with sixteen styles including argyle, polka dots, and stripes. Before placing our full order we ended up adding solid black socks because of Mari’s intuition and this proved to be a great idea.

Original template/design file (left) and the final product (right)

how-we-started-a-18k-month-fun-and-colorful-groomsmen-socks-company

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Mari & Matt McNamara, on starting No Cold Feet LLC ($17,800/month) full story ➜

28. Sales training ($20K/mo)

Jonathan Pritchard started Like A Mind Reader, a Sales Training business. They are now doing $20,000/month.

  • Location: Chicago
  • Revenue: $20,000/ month
  • Started: over 37 years ago
  • Founders: 1
  • Employees: 1

Whenever I’m sitting down to design a show or presentation I work backward. The first thing I do is ask myself, “At the end of the experience, what do I want my audience walking away feeling, remembering, or doing?”

I have to define what impact I want to have before I can even start figuring out how I’m going to do it.

My first shows were quite scattered without much focus. But each engagement gave me another set of data to use towards refining my approach, delivery, timing, etc. With enough iterations and time I got enough experience behind me to be truly “world class.”

how-jonathan-pritchard-went-from-magician-to-building-businesses

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Jonathan Pritchard, on starting Like A Mind Reader ($20,000/month) full story ➜

29. Design services ($800/mo)

Abigail Butler started Chirps & Cricket Design Studio, a Design services business. They are now doing $800/month.

  • Location: Denver
  • Revenue: $800/ month
  • Started: over 5 years ago
  • Founders: 1
  • Employees: 0

It took me approximately five or six months to develop my first line of stationery products. I began with a small set of note cards, about ten in all, and eleven wedding invitation suites.

I began with finding the two companies that I wanted to buy my paper from (almost) exclusively – Paper Source and Envelopes.com. What I liked initially about these companies was

1) the quality of the product themselves (for example, the thickness and durability of Paper Source envelopes is hard to beat) 2) pricing – these two companies sell their products at affordable costs, without compromising on quality, offering trade industry discounts and wholesale purchasing 3) variety – both companies offer a wide range of color and paper weight choices.

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Abigail Butler, on starting Chirps & Cricket Design Studio ($800/month) full story ➜

30. Garden tool ($10K/mo)

Michele Morgan Morton started The Maxbit, a Garden tool business. They are now doing $10,000/month.

  • Location: Mississippi
  • Revenue: $10,000/ month
  • Started: over 4 years ago
  • Founders: 1
  • Employees: 3

The doors closed one after another on trying to license the idea, but I continued to keep the prototype before potential customers.

We explored out of the country manufactures as well as all over the US. Then it happened! We met with a potential maker in our own state and he accepted the challenge to produce the tool - which still did not have a name.

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Michele Morgan Morton, on starting The Maxbit ($10,000/month) full story ➜

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Starter Story,   Founder of Starter Story