Today's Guest

We’re taking a look back at some of the best Winning on Main Street episodes from 2021. Each week we strive to deliver content that will help small businesses overcome the challenges they face and realize opportunities. These were some of your favorite guests and the powerful insights they shared on how to become a better and more successful small business owner. We hope you enjoy and we look forward to bringing you more great content in 2022.

Episode Summary

Jeffrey Feldberg increased the value of his business by 10x in 2-years before selling. Jeffrey shared, up to 90% of liquidity events fail, and most of the time they fail due to a lack of preparation. However, even for the remaining 10% of events that are “successful” 50% to 100% of the deal value is left on the table. Given that selling your business is generally one of the largest most important transactions it pays to get it right. Listen to the full episode

Mike Jesowshek showed us the sexy side of taxes, while sexy and taxes might not sound like they belong together here is what Mike had to say. The biggest mistake most people make when it comes to taxes is failing to plan. Most people only think about taxes during tax season, which means they are missing out on tax strategies they could leverage throughout the year to minimize tax liabilities. Filing returns should be the last step of your tax strategy, not the only step. Listen to the full episode

Mike Michalowicz had early success building and selling businesses only to lose it all on a handful of businesses that failed to achieve profitability. Mike shared, 83% of businesses globally are in check to check survival which leads to a cash crisis. That doesn’t mean entrepreneurs are incapable of being profitable but rather identifies a problem in the underlying business model we all learned. We’re told profit comes last, sales minus expenses equal profit. So we flipped the formula to be sales minus profit equals expenses so that profit is baked into every transaction from the start. Listen to the full episode

Chris Miles discussed the “popular” topic of cash flow and how the difference between making and not making in your business hinges on understanding this not-so-popular topic. Here is what Chris had to say, a lot of people think cash flow and revenue are the same but they are not. When you boil it down cash flow is your profit, it is what is remaining after you’ve covered expenses. The more cash flow your business has the more options you have to invest in and grow your business. Listen to the full episode

Jim Johnson built and sold a successful contractor business and then started a coaching business to help other contractors achieve their version of success. Jim shared, the two biggest areas he’s seen that cause a business to fail are leadership and financials. If you are leading a business you must be continually honing your leadership skills. The same goes for business acumen, while you don’t have to become a finance expert you need to level up your knowledge on the topic. If you want to achieve financial freedom and your business to thrive you cannot ignore these two areas. Listen to the full episode

Patrick McFadden was an audience favorite at the Thryv Connect conference and an expert in small business marketing. Here is what Patrick had to say, there is a process for how you should conduct marketing and a strategy for how to implement that process in your business. It starts with understanding who your ideal customer is, what problem you are solving for them, the customer journey they take when looking for a solution, and what makes your business different from the competition. Once you have the answers to these questions you will go from marketing being an expense to marketing being the fuel that grows your business. Listen to the full episode

Jeffrey Shaw made a name for himself as a portrait photographer for the rich and famous. Now he coaches other business owners on how to find clients that are willing to pay for the level of service you deliver.  Jeffrey shared, dive deep into what your best at and then ask the foundational question, what type of clients see value in that. Any product or service is sellable to someone, your job is to figure out who that person is and then market to them. Listen to the full episode

Melinda Emerson, AKA the SmallBizLady, is one of America's leading small business marketing experts. Here is what Melinda had to say, in any business a successful marketing campaign starts with defining who you want to reach. Then you figure out what platforms and media they use, then you target your marketing efforts in the place your ideal customers are already engaged. Once you get a prospect interested you plug those leads into your CRM and automate as much of the follow-up communications as you can. Listen to the full episode

Ross Kimbarovsky helps small businesses establish their brand identity and believes it is critical to building credibility and trust with your customers. Ross shared, every business has a brand, and building your brand a little each day will not only help you attract new customers but will lead to more referrals and repeat business. Listen to the full episode

Erin Fults guides her clients towards a better brand image by following the Story Brand principles. Here is what Erin had to say, most brand messaging is all centered around the business, they are the hero of the story which is a turn-off for customers. Rather what you should do is talk about the problem your customers have and how you help solve that problem. Listen to the full episode

Bernadette Doyle is a small business expert from Ireland that coaches businesses on how to improve their sales pitch, even if they hate selling. Bernadette shared, her primary business model is centered around helping her clients get more clients and make more money. While you might think if you had more clients you would make more money that isn’t always the case if you have the wrong pricing model. Listen to the full episode

John Jantsch is a marketing consultant, speaker, and best-selling author behind Duct Tape Marketing. Here is what John had to say, a good marketing plan starts with a strategy. You first determine who’s in your target market and then you create messaging that speaks to the problem you will help them solve. For marketing tactics to gain traction you need to become known as the best at solving a particular problem. Listen to the full episode

Brian Moran launched the Small Business Edge to provide advice and insights that help entrepreneurs manage and grow their companies. Brian talked about the value of having a business GPS plan, especially when things go off course. Brian shared, we often play the “what if” game with clients to help them think about in advance what they would do when things go off plan. While it can be frightening to think about, it is much less frightening when you have a plan in place to overcome those challenges. Listen to the full episode

Tim Berry is an advocate for small businesses and a proponent for creating a lean business plan to help businesses run better. Here is what Tim had to say, a lean business plan includes your strategy, tactics, assumptions, and essential business numbers. However, the power of the lean business plan is not that you create one but that you review it regularly. No matter how pretty-sounding or looking your business plan is if it doesn’t change your business for the better then it’s not a very good plan. Listen to the full episode

Mitch Joel has been called a visionary, digital expert, and community leader. Mitch talked about the power of creating great content and how small businesses need to leverage technology even more in a post-COVID era. Mitch shared, COVID pressed upon all businesses to become more localized in their customer offerings. This helps level the playing field for local businesses because they know their local markets best. Listen to the full episode

Bill Flynn has spent years studying why businesses fail and how to turn it around by unlocking growth and increasing the odds of success. Here is what Bill had to say, start a business by falling in love with the problem you want to solve and the customer that experiences that problem. Starting a business can be hard and some days suck, but when you can get energy from solving a customer’s problem you will get out of bed the next day and try again. Listen to the full episode

Roland Frasier made a career out of buying and selling businesses and is convinced most businesses are leaving money on the table by not maximizing existing client value. Roland shared, don’t spend all your time getting ready to get ready, and don’t take money from other people to get started. Having to be scrappy in the early days to find the business model that works will force you to iterate faster than if you’re sitting on a pile of cash. Listen to the full episode

Jay Samit is a dynamic entrepreneur and intrapreneur who is widely recognized as one of the world’s leading experts on disruption and innovation. Jay talks about how one day every business will face disruption and how every business should think about themselves as a high-tech start-up. Here is what Jay had to say, we are living in an era of endless innovation and you can choose to either be terrified by that reality or excited. So why not try to live a life of purpose and fulfillment by pursuing what is meaningful to you. Listen to the full episode

Dave Menz grew up in poverty and overcame tremendous obstacles to become a successful entrepreneur, running the multi-store, multi-million dollar chain of laundromats. Dave’s rags to riches story is inspiring to say the least but also something he believes is possible for anyone. Even as a young kid Dave found inspiration in the stories of other successful entrepreneurs that started with nothing and built a business from the ground up. So if they can do it why not me and why not you. Listen to the full episode

Michael Haynes has worked with companies ranging from micro-businesses to large corporations in Australia and Canada. He talked about the importance of working on your business not just in your business. Michael shared when it comes to product-market fit, the simplest way to think about it is are you offering products or services that customers want to buy. What problems do they have and what types of solutions appeal to them. Listen to the full episode

Rieva Lesonsky has been writing small business content for years that help entrepreneurs

start and grow their businesses. Rieva shares why small businesses need to leverage software to modernize and automate their client experience. Here is what Rieva had to say if you don’t accept digitization you are going to get left behind. What you have to realize is other businesses do what you do and the ones that digitize will be the ones that attract new customers and retain the ones they have. Listen to the full episode

Ramon Ray is a leading expert on small business success and a best-selling author. Ramon gives us his take on what it means to build your personal brand and create a foundation of processes. Ray shared, for a business to grow you need to map the right systems on top of great processes. When leveraged correctly technology helps you create a more seamless customer experience and deliver better service. Listen to the full episode

Steve Strauss is a best-selling author, small business columnist, and thought leader on small business topics. Steve talked about how implementing systems and processes now will not only help you run the business better but maximize the value when you’re ready to sell. Here is what Steve had to say, the most successful small businesses out there have one thing in common, they are leveraging technology to make things faster, better, and more profitable. Listen to the full episode

Tommy Mello scaled his business from $50k in debt to a multimillion-dollar company. Tommy shares the secrets he’s learned buying and scaling businesses and how you can leverage technology to get your life back and be more successful. Tommy shared, software is the key element behind scaling your business and unlocks exponential growth. When I look at buying a company I want to see they’ve adopted technology in some way before I’ll even consider purchasing them. Listen to the full episode

Those were all your favorite episodes from 2021 and we look forward to bringing you more great content and helpful insights in the year ahead. Listen to the full episode

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