My Biggest Business Milestone (So Far) — Experts Weigh In

Every small business goes through a number ups and downs throughout its life. We wanted to know what small business owners are considering their biggest milestones to be. Here’s what our small business experts had to say…

“I am a former U.S. Marine that’s constantly trying to reach milestones. The biggest milestone for Ena’s Driving School so far was opening up a second location in 5 years. 

My next milestone is to pass my first million dollar mark by the end of 2015. I can almost taste this milestone.” –Rajendra Hariprashad, Ena’s Driving School, Inc.

“My business Think Traffic is an online marketing agency. I started out as a freelance consultant, but my biggest milestone to date has been taking on my first members of staff. If took a big leap of faith because employees are expensive, so I had been trying to cope for a long time doing everything myself. I now have 3 employees and overall the experience has been very positive, I can now specialize and give all of my clients a much higher level of service. By taking on staff with existing experience I have also been able add new services and improve existing ones (we are doing much more social media management and PR work now). 

The biggest challenge of taking on new employees is probably the cost. You have to make sure you have enough work to justify the wages. I have had to work hard to train my new employees to a point where they can be mostly autonomous and now I am working hard to bring in more work so that the business can continue to grow.” –Alex Johnson, Think Traffic Ltd.

“We launched our enterprise CX analytics SaaS product (Decibel Insight) in 2014, noticing a gap in the market for a behavioral insights solution which served Fortune 1000 companies and fully supported agencies with in-depth reporting for their clients’ websites. 

Our biggest milestone to date has been broadening our operations from our HQ in London, by recently opening an office in New York City to accommodate the demand from the USA for our SaaS. Our startup has hit the ground running and we are incredibly excited in anticipation of reaching our next milestone!” –Ben Harris, Decibel Insight

“I started Peloton in September of 2014 after 22 years as a healthcare leader and executive. My biggest milestone isn’t about revenue or number of customers, but rather mindset. As an entrepreneur, one puts in a great deal of effort to establish a successful business. Therefore, it’s easy to make it all about yourself. My a-ha moment and milestone came when I realized that my focus needed to be on my customer. They are hero of the story. I am not. I’m just a guide. This change was instrumental in driving more success. It was my biggest milestone to date.” –Michael, O’Brien, Peloton Coaching and Consulting

“I started Mobovivo in 2009. In 2014 the company of about 20 people delivered a #1 sports app that provided updates, replays, gamification, and access to behind the scenes moments for 2014 FIFA World Cup to hundreds of thousands of users in 6 languages and 18 countries for ESPN, FIAT, Intel. This milestone was reached at the same time as our team delivered the top rated TWC Sportsnet app for the NBA and months after providing a mobile experience for the Academy Awards focused on gamification and behind the scenes.” –Trevor Doerksen, Mobovivo

“I hit my company’s biggest milestone 4 years ago when I found UpWork and hired a programmer. The milestone was to start adding technical staff. I had been doing all of the programming work, and was having trouble letting go and working ON the company instead of working IN the company. UpWork (formerly oDesk), is an online resource to hire freelance contractors. It was a huge find for me, because the freelancers were rated by the companies for whom they had worked. They have eager and well-qualified freelancers worldwide. Technical job postings always get many responses. Since then I’ve become much more a president, and have hired at least 10 other people via UpWork. My company’s earnings have grown an average of 33% each year. It was a major breakthrough.” –Cynthia Worden Lee, Performance.net 

“Our biggest milestone to date has been reaching the point when we could no longer do it all in house. Realizing we had reached our maximum capacity with accounting and account management was pretty exciting as well as scary. 

Our realization happened a bit later than it should have and it was quite the task to right the ship and get things back into order. 

However, now having the right professional handling a large part of our core competency has freed up so much time and energy that we can pour into other areas of business development and expansion.” –Elyse McNabb, Nourish with Style 

“So far the largest milestone NiLi has reached is making our first sale. While we have made many more since then, the first is by far the most important. It shows that we have completed the full cycle of proving the concept of NiLi and that it is useful for our customers. Once you have completed the full business cycle, and have proven concept, it is then a matter of repeating that process and scaling it (Easier Said than Done).” –Dylan Osborn, NiLi

“I hit an exciting milestone with my business, Adore! About 5 months ago I started my own online boutique for girls ages 2-14, adoreyourcloset.com. My story was featured recently on the front page of the local paper. My boutique is unique because my mission is not only to make girl’s feel beautiful through my clothing, but also to feature special needs models and be active in the community and with other women entrepreneurs. With a strong social following that I’ve gained organically in 5 months, this is only the beginning and I would love a feature!” –Holly Diederich, Adore

“We hit our biggest milestone recently, when we first offered our employees health insurance – which also meant offering myself health insurance. This is a great milestone to hit when you can afford it. Your company has made it beyond merely fighting for survival, and you can start building a compensation package that will attract good workers. You can spend time and energy not just on the business, but on creating a great organization. And it gives the people that work for you a sense of progress and a clear sense you care about your team.” –Marc Prosser, Fit Small Business 

“The first major milestone was surviving 9/11. A few weeks after founding the business, my partner and I were in the World Trade Center when the first plane hit. It changed our whole business philosophy to helping other businesses survive. In 2012 we became a Worldwide Microsoft Partner of the Year. That same year we helped our customers recover quickly from Hurricane Sandy, perhaps our proudest moment. Every year we have grown by double digits, an annual milestone. Making the Inc. 5000 list 6 times is another. Carl’s opinions are informed by 14 years of consulting with businesses in the NYC area and internationally.” –Carl Mazzanti, eMazzanti Technologies

“The biggest milestone for my marketing agency was establishing recurring revenue. For the first 7 years in business we worked on a contract by contract basis. While we were able to grow year over year, there was always a concern about where our next project was coming from and it was a constant roller coaster ride. We could never see more than a month or two into the future and it really stunted our growth and decision making. Now, Brolik has both project-based and recurring revenue services. This has led to a more balanced business and a projectable future.” –Jason Brewer, Brolik

“The biggest milestone I’ve hit since starting my business in March of 2014 is reaching 150 online sales in one day. It was celebratory for me because like any new business there usually isn’t am immediate boom in sales. Though we’ve had some mountain peak, valley low moments in regards to our sales, that particularly was a very accomplished moment for me.” –Tiffany Sartor, Posh Peyton

“The biggest milestone we’ve experienced on the road to business growth is increase sales with higher conversions (50% and more increase in income). I’d like to mention that it is very important to plan out the milestones you want to achieve. It gives you something to strive for and motivates you when startup gets hard. And don’t hurry up, the common mistake of most entrepreneurs is trying to force growth prematurely.” –Emily Brown, Get Academic Help   

“Since opening my business the biggest milestone I was able to achieve was hitting my target goal revenue for a year. It was a long and difficult journey, but nothing can compare to the joy and satisfaction of reaching my goal. There were days where I could not see the light at the end of the tunnel but determination and motivation held me together. Every business owner should set a milestone for different aspects of their business. Achieving your milestone goal can be a great way to rejuvenate your passion for your business.” –Lisa Chu, Black N Bianco Children’s Formal Wear

“The biggest milestone we hit since opening is when we started to work with fortune 500 clients. It gave us the necessary market validation we needed to expend our business.” –Tatsuya Nakagawa, Castagra Products, Inc. 

“It may not sound like much, but our biggest milestone thus far has been making it to the one year mark successfully. 1 in 10 small businesses fail in their first year, and I knew the odds were stacked against me. I am a 24 year old recent college grad and only invested $600 in my company. I was thrilled when we made it to the one year mark with six employees and nearly $75,000 in revenue–definitely a milestone to celebrate.” –Bonnie Treece, The Brain Domain

“My biggest milestone is happening right now! I’m just hitting 25 years in business. Same job. Same outfit. Same profession. And, somehow, I still love it.” –Richard Laermer, RLM Public Relations

“After four tumultuous years of building my startup with the wrong partners, lots of bad decisions and some major rookie mistakes, I was determined to find a way to take my business to the next level … and what better way than to apply to ABC’s Shark Tank. In September of 2013, I found myself walking down that scary shark infested hallway into a stare off with 5 of the harshest millionaire investors in the world. After getting shot down by all five Sharks, I looked them in the eye and said, “Trust that you’ll all see me again.” Since the Shark Tank aired in February of last year, I found the missing links from years before and we’ve raised 5 times the amount I’d sought on the show and I’ve gotten a CTO on board who’s helped facilitate and finance the new face and technology behind the newly pivoted Cheekd mobile app.” –Lori Cheek, Cheekd 

“This year was a defining year for Corso Law Group as we completed our firm’s first expansion, into Houston, Texas. We put in years of hard work to establish Corso Law Group in Scottsdale, Arizona focusing on key cases that made a difference in our state and to our clients. Our team then carried this work ethic and focus into the Houston market, and we proudly opened Corso Law Group in Texas this past summer. What’s even more exciting is that the new firm is thriving in a new environment and we’ve continued to have success in our home base of Scottsdale.” –Christopher Corso, Corso Law Group

“Since OncoSec opened its doors in 2011, our greatest milestone has been uplisting to the Nasdaq Capital Market this past summer. By listing OncoSec’s common stock on a national securities exchange, we have been able to increase the company’s visibility, raise awareness of our technology beyond the scientific community, and operate in a marketplace that aligns us with our peers in the cancer immunotherapy field. As a Nasdaq-listed company, we are now in a better position to continue to advance our technologies with the goal of one day benefiting cancer patients everywhere.” –Punit Dhillon, OncoSec

“We started out about ten years ago as a carpet cleaning shop during the depths of the Great Recession. And we started to fail almost immediately. Our founder decided to take on more jobs and one of these was subcontracted from a restoration company. He realized that he could help more people and do better for himself if he were a part of the restoration industry and not just a carpet cleaning operation. 

Since that change we have grown significantly. Then we incorporated a different marketing model that has completely changed the course of the business. Instead of partnering with insurance giants for their customers, we market directly to consumers with smart devices in their time of need. 

These two changes have allowed our carpet cleaning operation to grow into the restoration industry and evolve from one shop to more than fifty locations in all major cities around the country which collectively did more than $27 Million in sales last year alone.” –Alexander Ruggie, 911 Restoration

“Having turned down early investment offers because they required us to offshore manufacturing (proudly our product is handcrafted in the USA), our biggest milestone has to be bootstrapping and growing our business through retained earnings (so no paycheck for 2 years) to where it can now comfortably support my business partner and I along with a few employees. The other major milestone is growing our direct to consumer model to where brick n mortar distribution is no longer necessary (although on the radar for 2016). Now, with customers in every US state and over 80 different countries, we continue building one customer at a time!” –Billy Thompson, Thompson Tee Inc.

“I recently launched my start-up Popwish. We design and handcraft unique Pop up greeting cards and sell them both online and in retail. I have attached a picture for you to get an idea of our Popwishcards. Our milestones were 100 customers and 60% of initial investment returned in 5 weeks of operations. After launching about 5 weeks ago, we have had more than 100 customers, which returned more than 60% of our initial investment.” –Mark Oldenburg, Popwish

“The biggest milestone I hit was my first 10k month, much sooner than predicted. It seemed like once I hit that, I was off and running. I rewarded myself with a continuous brewer Kombucha maker from www.kombuchakamp.com. Definitely a splurge, and I deserved it.” –Marcey Rader, Marcey Rader Coaching, LLC

“Starting with a small business, one of the biggest worries is attracting the right niche talent for your enterprise. As a business with a focus on hiring people with disabilities with technology skills, we were worried we’d have a hard time attracting talent. Our milestone for five years in business was to meet the national average of 20% employment of people with disabilities. Now, six years later, we’re cruising in at over 85% of our workforce having a disability. It’s a huge win for us, and one that we share with other organizations looking to hire people with disabilities. We are hoping to keep growing, and have that number increase. Beyond statistics, we have also been happy to see that number grow nationwide in business across the country.” –Dana Marlowe, Accessibility Partners

“While we have been fortunate to achieve several wonderful milestones, I would definitely choose having one of our products featured on The Today Show. Our very trendy and affordable accessories were found to be the perfect fit for the show’s Luxe for Less segment and it brought an incredible amount of attention to our website since we were not only featured on air but also on the show’s website.” –Sandy Bodeau, Sira&Mara Accessories   

“The biggest milestone I hit with SME was getting to the 15 year mark. We 
beat the odds, especially given the nature of the travel and event industry 
since 2001. 

Creating a second company; SME Displays, which has an international focus, 
has been a huge leap forward for us. It takes the comfort of owning a 
business right out from under your feet as international business is a whole 
new thing. 

Being honored for my contributions to the industry, as a female and as a 
leader and mentor have also been milestones. I will never stop learning but 
I finally know enough to be a recognized resource on a variety of levels.” –Christy Lamagna, Srategic Meetings and Events, SME Displays 

“The biggest and most important was when we were no longer dipping into our savings to meet our month to month bills. It was then we realized that we truly had a viable business plan and job security!” –Jeff and Deadrea Clemmenson, MiPhone Doctor

“Our biggest business milestone was winning a major contract with the Arkansas State Police. We were going up against 18 other companies with two of them being much larger and older than mine. One has over 20 years experience in law enforcement transcription, the other 10 years. They were the gold standard in law enforcement transcription until I forced my way onto the scene. It was a big win!” –Ben Walker, Transcription Outsourcing LLC

“The biggest milestone I’ve hit as an entrepreneur is seeing my own staff not only having features written up about them in international publications, such as the Miami Herald and Scholastic Magazine, but also having staff interviewed and quoted in major international newspapers, such as the South China Morning Post. Whilst I personally have received regular media coverage over my 7 years growing the business, to watch my staff start to receive such press is truly a milestone and also makes me glow with pride. It’s a true testament to the amount my employees have grown professionally during their time at InTouch. They’re now experts and thought leaders in the industry, and they do a stellar job of representing our company and our brand each and every day.” –Andrew Reich, InTouch Manufacturing Services