How to Start a Business

So you want to start a business? 18 years ago I quit my cushy finance job to follow my passion by going out on my own. It was scary and I had many failures, but I never once regretted my decision. I discovered a passion that I never knew existed and that made the sleepless nights and lean years totally worth it - it changed my life for the better. 


Launching a business will give you a crash course in ideation, branding, marketing, social media, building a website, keeping the books, buying a domain name, incorporating, sales, and sometimes failure. Learn from the failures. 


If you’re jumping into a new field then it’s an excellent way to learn the industry. When I launched Research Connect in 2001 it allowed me to get out of finance and into the online startup world. Previous to Research Connect I interviewed at a handful of internet companies, but every company turned me down for the exact same reason - you’re a finance guy with zero online experience. They were right so I decided to get that experience on my own. I was tired of waiting for someone to tell me when I could have job satisfaction - I was going to create it for myself. Research Connect ultimately closed a few years later, but it was a tremendous learning experience.  


From that closure I learned to focus on a niche, rather than trying to solve every problem, and I brought that knowledge with me to my next startup. 


My advice; focus on a specific problem or need. Keep things as simple as possible at launch so it’s as simple as possible for people to understand. Over time when you’ve built a foundation you can start tackling other problems that correlate with your mission.

Business Ideas

Come up with a business idea that’s unique and authentic to you -  you’ll never stand apart from the pack by doing the exact same thing as everyone else. When I created the logo for Stride for Stride I didn’t want it to look like the typical running logo. I knew we would never stand out among thousands of runners by looking like everyone else. It’s crucial to be different.


Business ideas usually come to me when I turn off all distractions, and experience something new. To get creative I often; 


  • Turn off my phone

  • Shut down my computer

  • Go for a walk somewhere I normally don’t walk

  • Take a scenic drive on a new route

  • Read a book

  • Watch/read good (positive) news


Sometimes business ideas come easily and other times you can’t think of anything new or creative. For me, ideas often come in waves and I’m rarely creative when I’m stuck in my normal routine. Walking through a new neighborhood, running a different route, or getting lost on a long drive can generate new experiences and new perspectives that your normal routine doesn’t generate. 


Some business ideas come easily; I created Heart to Cart in 24 hours after being inspired by a story about Tyler Perry buying groceries for seniors in two hard-hit cities during COVID-19. Other ideas take time; I knew for a year that I wanted to do something to increase diversity in races, but I didn’t know specifically how to accomplish that. It wasn’t until the summer of 2018, when I turned off my phone and went on a two week road trip up the coast of California, that the idea came to me. Those two weeks allowed me to clear my head of social media and generate creative ideas from seeing and doing something new each day. I actually created two social impact companies during that trip - the second hasn’t been launched yet. 


During that trip I also read two incredibly inspiring books that challenge you to create a social enterprise or charity for social good; Start Something that Matters and The Promise of a Pencil.


And that brings us to starting something that matters.

Social Impact - Social Good

I firmly believe that every company created should have a positive impact. I’m not talking about donating a few percentages to charity each year. I’m talking about baking social good into the core DNA of your company - having a purpose that is the root of everything you do. 


You do not have to sacrifice profit for purpose - you do not have to choose one or the other. You can do good and make a good living too. 


There are thousands of successful companies that prove social good is good business. TOMS donates one shoe for every shoe purchased, Warby Parker does the same for eyewear, and Bombas donates a pair of socks to the homeless for every pair sold. 


When Stride for Stride launched it was a social enterprise that donated $15 for every singlet sold to purchase race bibs for low-income runners. 


The companies mentioned above are huge organizations, but you don’t have to be a million dollar organization to make a difference in your life and the lives of others. Look around you and look at your community to figure out how to make an impact. Today, companies that have a social impact are trusted more and frequented more than mercenary companies looking to stuff their pockets. 


Doing good is good business. 

Charity - Nonprofit

Flutter was a social enterprise that I created in 2015. It was an S Corporation (Inc.), but it’s core mission was to raise money for local (Boston) charity via $10 donations. Not only did we raise $125,000 for charity, but we (Steve Callan & I) also created a profitable business. 


With Flutter I worked closely with numerous small charities, and it was this experience that gave me an invaluable realization; non-profit founders are just as entrepreneurial as startup founders, they just measure success differently. That realization had a profound impact on me and ultimately led me to create my first 501(c)(3) public charity - Stride for Stride.


I highly recommend starting a charity or creating a charity that compliments your social enterprise. Many people think that social problems are so massive that they can’t make an impact and are therefore discouraged from doing anything about it. They’re wrong. 


You don’t have to save the world to make an impact in this world.


Start small and figure out a way to make an impact in just one life. I launched Heart to Cart in April 2020 to help those who were suffering the most during the Coronavirus Pandemic. We can’t afford to feed the world, but we did make the lives of 130 families a little bit better by sending them a $100 supermarket gift card. Heart to Cart was so easy to launch that anyone can create their own version - please do. 


What if 100 people created something similar in their own community with just $500 in donations? That’s 500 families whose lives were made better because of you. I call that making an impact in this world. 


I can’t help everyone, but everyone can help someone. That is how we change the world.


In order to launch a successful business you must be passionate about what you’re doing. If you’re not passionate then your business is bound to fail. That’s why it’s essential to find something you love, and not do it just for money. 


I love running, and Stride for Stride - a running organization that buys race bibs for immigrant, BIPOC, and low-income runners - fits perfectly into my passion. 


I love my hometown of Boston, Massachusetts and BostonTweet was created because I was worried that the city would suffer during the 2008 recession. 


It’s important to take your passion and figure out ways to make it better. I run a lot of races and two things I noticed when running a race were; 1) races are expensive, and 2) races lack diversity. From this I came up with the very simple concept of Stride for Stride; purchase race bibs for those who can’t afford to run, which in return will help make races more diverse.


In 2008 my concern was restaurants would suffer during the 2008 recession. How can I help? The decision was to launch a service that promoted local businesses during the recession. 

Keep it Simple - Branding

I’m a firm believer of keeping your business as simple as possible - don’t over complicate things. You should be able to describe what you do, and people should be able to understand what you do, in one sentence. 


Stride for Stride buys race bibs for low-income runners. Heart to Cart buys supermarket gift cards for people who can’t afford to eat. Both are succinct and easy to understand - make sure your business has a one-line mission that is easy for you to say and easy for potential customers to understand.


This brings us to one of the most exciting aspects about starting a business; branding. Coming up with a name, a mission statement, and one-liner is the first step in giving your business life. Once you have these three then you can start thinking about your logo. A logo is the birth of your business. It’s what people will see first - it’s what will draw them in for more.


One thing I highly recommend is turning off your phone, closing your laptop, and jotting down your ideas in a paper notebook. I always use an old school marble notebook to jot down my ideas, but any old-school paper and pen works. 


Turning off technology allows you to focus on nothing but your business idea. Spend the time to come up with names, designs, and your mission statement. Come up with as many names as possible and don’t worry about writing a verbose mission statement at this stage. The more familiar you become with your business the easier it will be to whittle that mission statement into one impactful sentence. 

Buying a Domain - Web Hosting

One of my favorite pastimes is to search available domain names. 


All domain name registrars have a “find your domain name” search box which enables you to search dozens of suggestions based on the name you’re looking for. Don’t get frustrated. Finding an available domain name is actually quite challenging, especially if you want a .com name. And don’t forget to make sure your business name is available on social media platforms like Instagram, Twitter, TikTok, and YouTube.


I personally use GoDaddy and Directnic to search for and register domain names - the latter I’ve been using since 1997. 


In the past I’ve built very complicated and very expensive internet databases (Research Connect, Bizak & Flutter) that required hiring a developer. That route always takes a lot longer and costs a lot more than previously expected. Unless you’re building a complicated internet database then I recommend building the site on your own. Publish your website and see how the world responds to it before spending a ton of money. Your business will evolve over time and because of that I always recommend putting out a minimally viable product (MVP) to learn what your customers want before you spend the time and money trying to guess what your customers want. You will be shocked by how much your business evolves over time. Embrace feedback and make changes based on that feedback, but always stay true to your mission and the purpose of why you started your business.


I highly recommend using a website builder like Wix, Shopify, or Squarespace to create and launch your business website. All three platforms are simple to use without any coding experience needed - you basically drag and drop. They’re terrific. All three website builders also have ecommerce tools so you can quickly and easily build an online store that accepts online payments. For only $15 to $25 per month you can build your own professional website in mere hours.


Stride for Stride (website & ecommerce), Bostontweet (website), and Heart to Cart (website) are all built using Wix. I’m not a tech developer so going forward all my future ideas will be outlined so I can launch the website on my own. It saves time, money, and it gives YOU total control.  

Get a Personal Email Address

If you’re running a business do not send emails from an @gmail or even worse an @aol account. Set up a personalized email address @ your website. All the web hosts mentioned above offer this service, but I prefer creating a G Suite account with Gmail hosting for your business email. The basic service costs just $6/month per user. 

Business Formation

If you haven’t noticed I like bootstrapping my ideas and that includes saving money on a lawyer when incorporating or filing for 501(c)(3) status. 


I’ve used LegalZoom since 2003 to create a handful of S Corporations and most recently to file Stride for Stride as a 501(c)(3) public charity. Applying for 501(c)(3) status gives your business the tax benefits of a non-profit corporation and it allows donors to make tax deductible donations to your charity. 


Creating an LLC or Corporation is relatively easy with your legal status and Employer Identification Number (EIN) usually approved within hours. Creating a non-profit takes a lot more paperwork and a lot more time - usually 6+ months for the IRS to approve your 501(c)(3) tax status, if approved at all. 


Don't forget that creating a corporation requires filing corporate taxes each year. Nonprofits that have gross receipts under $50,000/year can easily file Form-990 N (e-postcard) online. 


The main benefit of creating a corporation or an LLC is to protect the assets of the business owner so he/she is not personally liable for corporate debts and liabilities. 


In addition to securing your URL, it’s also important to perform a free trademark search with the United States Patent and Trademark Office (USPTO) to make sure you’re not infringing on someone else's trademark. Please note; your name, or a variation of your name, is likely already used by somebody else. That does not mean you can’t use that name or a variation of that name. As long as your name doesn’t create confusion with the other mark then the USPTO will likely approve your trademark. Confusion is created when you’re selling the same exact product or service with the same name as the other company already trademarked.  


Similar names can live in harmony; Delta Dental, Delta Airlines, and Delta Faucet Company are all separate companies that peacefully coexist because their products are different enough that they don’t cause the consumer to be confused. As long as you’re not performing the same exact service or selling the same exact product then you’re likely okay using a similar name. 


Try to be as unique and creative as possible in every aspect of your business, including the name - it will help you stand apart from the pack. 


You do not have to file a trademark in order to launch your business or website - it’s just another level of protection for your business. If you think your name and your service are too similar then it might be best to chat with a lawyer. LegalZoom also offers trademark filing starting at $199.

Banking - Online Payments

Opening a separate business account is essential for keeping personal and business funds separate. Every bank offers corporate checking accounts with various monthly maintenance fees - research what bank is best for your area. If you’re a non-profit then there are numerous banks that waive that monthly maintenance fee. Eastern Bank is one example in the Greater Boston area that offers free banking for nonprofit organizations. 


For accepting online payments, or accepting credit card payments offline, you can’t go wrong with PayPal, Stripe and Square.


PayPal offers discounted translation rates (2.2% + $0.30 vs. 2.9% + $0.30) for confirmed 501(c)(3) public charities with no monthly fees. 


If you’re accepting online payments via an ecommerce website then Stripe and Square are both top-notch online payment processors. Square is best for collecting in-person credit card or Apple Pay payments via the Square app - for example collecting payments at a farmers’ market. 


Square charges 2.6% + $0.10 for those in-person payments, and 2.9% + $0.30 for online payments. Visit How Square’s Processing Fees Work for a breakdown and explanation of their fees. Stripe charges 2.9% + $0.30. 


Stride for Stride uses Square for our ecommerce store, Stripe for offline payments, and PayPal for fundraising. Speaking of fundraising; Give Lively is a tremendous resource to help nonprofits fundraise, and it’s entirely free.

Launching a Website

Launching your website is one of the most exciting days for a small business. Months of planning have finally come to fruition and you're ready for the world to see your creation. Friends and family usually support you on day one, but be warned; that initial launch traffic will likely die off in a week or two, but don’t get discouraged - it takes time to build your brand, and to create a community that trusts you. 


I launched Stride for Stride on November 21, 2018, and the first few weeks were terrific - friends were congratulating me on launch, buying our running gear and posting about us on social media. Then that initial buzz stopped. It’s scary and frustrating, but you have to keep plugging and believing in your idea. Over time you’ll build a community of supporters who value your product or service because of what you’re offering, not just because you’re related to them. 


Stride for Stride is now two years old and I feel like we’re just hitting our stride. [pun intended]


The most important thing to remember about starting a business is to be passionate about what you’re offering. Without passion you’re bound to fail. You can’t expect customers to be passionate about your brand if you’re not.  That’s why believing in what you’re doing is essential for small business success. 

Marketing - Social Media Marketing

Your business is launched, your website is live, and your door is open to customers. Now the real work begins. Marketing is essential for success, and you have to be able to adapt to feedback and the changing times - marketing now is much different than it was in 2019.


Being on social media is a must and you should have already created a Twitter and Instagram account many months ago. Each platform is different so don’t just push content from one to the other. Twitter is an essential tool for communicating with anyone in your field or for potential customers looking for your product. Twitter search is extremely valuable for companies offering business services, as is LinkedIn. Search for your keywords and engage with conversations in your field. Over time you’ll build a loyal community. Do not get wrapped up in how many followers you have - it’s quality over quantity. 


Instagram is more of a visual platform and it’s probably the best social media tool for companies selling a product or an image - Pinterest is great too. There are tons of resources online for mastering social media. I’ve always said the key to social media success is to know your market and communicate with them just as you would in the real world. 

Social Impact Marketing

My favorite type of marketing is social impact marketing - a marketing campaign that creates a positive impact and in return generates positive buzz for you.


Two social impact marketing campaign that I created for clients are:


#ShareTheLove - On Valentine’s Day, a local burrito chain asked customers to hand out free mini-burritos to those in need of a valentine on Valentine’s Day. We asked customers to give burritos to a total stranger, to a homeless person, to their favorite barista, to their Uber driver, or anyone who could use some love on Valentine’s Day. We gave each customer 5 free mini-burritos and asked them to #ShareTheLove on social. The campaign was a tremendous success; it created positive awareness for the business on social media and more importantly  it made a lot of people very happy. The only dollar cost to the business was getting their product into people’s hands.  


#CleanBoston - a social impact campaign that I created for a Boston-based cleaning company. Via social media we recruited 30 people to help us pick up trash in the Boston Common. It sounds like a dirty job, but when you recruit members of your community to help beautify your community then people will readily volunteer to help. Providing free lunch and free ice cream makes it even more enticing. In just 30 minutes we collected 5 large trash bags of litter, which generated a lot of social media buzz and some traditional media for the business. #CleanBoston was a successful marketing campaign that made our community better, that made the people volunteering feel better, and that created positive awareness about the company.


When you’re ready to launch a marketing campaign think if there’s a way that your marketing dollars can benefit the local community rather than funding billion dollar corporations like Google and Facebook - you and your customers will be far happier because of it. 

Make an Impact

Creating your own business is extremely rewarding, quite challenging, and at times absolutely terrifying. At the very least you’ll learn a lot and gain a ton of credibility. At best you’ll change lives. 


Make an impact, and good luck - Tom