Authentic Deal-Making Authentic Leadership Authentic Negotiating Deal-Driven Growth

A Deal-Maker’s Paradigm Shift

Jeff Dennis is the trusted advisor to the CEOs of fast growth companies, where he provides strategic and financial advice. He is a lawyer, serial entrepreneur, best selling author, and public speaker.His book, Lessons from the Edge, is a collection of stories by 50 entrepreneurs who share their biggest mistakes in business and the lessons that they have learned. He’s a sought after public speaker for audiences across the world. Here, he shares about the deal-maker’s paradigm shift that has helped him grow throughout his career.

Creative Problem Solving as an Entrepreneur in Residence

Jeff shares that, early on, he expected to take over the family business. After circumstances changed, however, he had to reinvent himself. This reinvention is what ultimately brought Jeff into the entrepreneurial space. 

Now, Jeff is an “Entrepreneur in Residence” with Fasken Law, one of Canada’s largest law firms. He helps them answer the question: How does a big law firm do business with these new tech companies?

These startups often have vast legal needs, but often few resources early in. Although some of them turn out to be unicorns that achieve wild success, many don’t. It’s clear, however, that they have legal needs. Part of Jeff’s role is to enable Fasken Law to meet those needs creatively. He considers himself to be part intreprenuer, as he’s building a small business inside of an institution. He’s part business advisor, as he does quite a bit of coaching and consulting within his work. And he’s part lawyer too, as a licensed legal professional! His journey certainly has been a “typical” lawyer’s journey, but he’s enjoyed his alternate career path.

Some of Jeff’s creative ability comes from a unique deal he crafted early in his professional life. It involved his family’s restaurant business, a massive theater complex raining debris on their patio, and a revenue guarantee that enabled them to sell at a profit. (Curious about the details? Listen HERE to get the whole story!)

Discovering a Deal-Maker’s Paradigm Shift

Prior to Fasken Law, Jeff went through multiple iterations of business. First, he thought of himself as a real estate guy. He was registered with the Ontario Securities Commission as a limited market dealer, and was syndicating real estate.

And then the market crashed. It seemed like everything Jeff was involved with was connected to real estate, and suddenly that was nothing but bad news. Rather than throw in the towel, Jeff set to work reenvisioning himself.

His realization? He was a deal-maker. This paradigm shift allowed him to see that real estate had been a commodity that he was making deals around. Rather than fixate on the commodity (real estate), his world opened up when he realized he could create deals in any sector, with any commodity.

Jeff has since done deals in mining, cosmetics, insurance, stocks & bonds, TV productions, franchises, and more.

If you’d like to hear more about Jeff’s thoughts on the “pound of flesh” required to take investor money in these types of deals, listen to the full episode here!

Always Growing

As he branched into deals, Jeff also worked hard to network and grow professionally. He joined EO (Entrepreneur’s Organization) and worked his way from local leadership to the international board. He wrote Lessons From the Edge, which became a bestseller and launched his speaking career. And he’s since traveled the world, speaking globally.

By using his deal-making skills as a springboard, Jeff has advanced personally and professionally throughout his career.

As he was writing and speaking, he also transitioned into angel investing. During this stage, he worked with early stage companies on commercialization and capital raising. Later, this experience would assist Jeff as he began crafting fixed-fee deals aligned with startup values and needs.

Creating Services & Products That Work

When Jeff talked about how a big law firm tends to deal with tech companies, the only word that came to my mind was “poorly”. Ultimately, law firms expected to operate with large hourly fees. And startups and entrepreneurs that were building tech companies couldn’t afford that.

There was an entire underserved market that was having to forgo legal representation, or deal with minimal legal counsel because it was out of range of their budgets. Jeff brought his deal-making experience to bear. Working within Fasken Law, he developed a concept for a fixed fee model that he knew would attract tech companies.

This creative solution required a great deal of negotiation. As a traditional law firm, they had to let go of “how it was always done” in order to try something innovative and new. From incorporating the company to creating shareholder agreements, creating employee contracts, and building employee stock option plans; Fasken Law became startup friendly.

Jeff shares that hundreds of companies from every sector came through these programs. Because they were structured as fixed-fee offerings that could be customized as needed, they were highly attractive to the startup market.

Ultimately, the deal-maker’s paradigm shift Jeff encountered early in his career has shaped his professional life ever since. There is power in making deals!

Listen to the full episode here!


Corey Kupfer is an expert strategist, negotiator and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author and professional speaker who is passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.

If you want to find out how deal-ready you are, take the Deal- Ready Assessment today!


Authentic Deal-Making

The Ultimate Comeback

Leukemia and bankruptcy are life-altering circumstances—Jeff Holst battled both of them simultaneously. For the average person, it is the ultimate test of strength and character, but Jeff is far from average. He has traveled all over the world, married the girl of his dreams, and he built a thriving law firm by the age of thirty. But when everything seems to be going as planned, adversity is often lurking around the corner. As Napoleon Hill says, adversity is often opportunity in disguise; it is no surprise that Jeff was able to find a silver lining. During his comeback, Jeff made sure he would never be in a vulnerable financial position again. He made sure that he had the freedom to live a fulfilling life and real estate was the answer.

Pick Your Niche and Find Your Stride

Jeff found his stride in the residential multi-family niche, though he has a couple commercial buildings as well. He focuses primarily on the B and C class, low-medium income housing. It is an investment approach focusing on positive cash flow from people who need a place to live and are looking to stay there for a decent chunk of time. Jeff recommends partnering with professional investing in these types of deals to anyone who is looking at real estate as an option for passive cash flow unless, of course, you are interested in owning and managing the buildings yourself which come with dealing with late night tenant calls from Tenants and other headaches. There are a lot of investors and property managers offering small interest in larger deals, which enables you to generate a passive income while delegating the headaches to professional property management companies.

Find the Right Deals

If you decide to invest in real estate, you need to pick a market you truly understand or it’s going to be a monumental struggle. The main challenge now is finding the right properties and the right deals, and figuring out what the current owners are doing wrong. You have to understand the weak points in the current management structure and identify inefficiencies in that market. Most of Jeff’s deals are self-financed, but a lot of the deal structure is based on each individual property. There is a lot of pressure when it comes to dealing with other people’s money; some handle it well and others don’t. But if this is something you are interested in pursuing, my podcast episode with Jeff Holst will provide you with a lot of valuable insights.

Listen to the Fueling Deals podcast episode featuring Jeff Holst’s interview about Financial Strength and Freedom Through Real Estate.

Corey Kupfer is an expert strategist, negotiator and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author and professional speaker who is passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.

If you want to find out how deal-ready you are, take the Deal- Ready Assessment today!

Authentic Deal-Making

Deal Design: Creative Real Estate Strategy

Gary Wilson developed a passion for drawing houses and architectural floorplans at just eight years old, but as Wilson grew older he would discover a much stronger affinity for the wealth that could be generated by them. His business sense and entrepreneurial spirit have been there through it all, and Wilson was always inspired by the simple exchange of providing quality service and getting paid for it.

The idea that you gotta wake up and show up to get paid is what shaped Wilson’s work ethic and prepared him to be a dealmaker as an adult. Wilson made his first real estate deal within a month of graduating college by assuming the previous owner’s VA mortgage, getting a second mortgage to refinance the seller’s second mortgage, then giving him a third note for his portion of the equity – so he put no money down. It was a very creative deal that was anything but conventional, and Wilson was even able to rent two rooms which paid for nearly all of his other bills.

The Pitfalls of a One-Size-Fits-All Deal Structure

From that point on, Wilson was determined to forge his own path outside of conformity. There are many ways to buy real estate but Wilson’s success is largely attributed to using the right strategy, at the right time, for the right deal. A lot of people tend to shove everything into a universal deal structure and that can be detrimental to their progress because every deal has the potential to be more lucrative if you get creative.

The ability to create tailored deal structures is a necessary component to becoming a great dealmaker, but mindset plays an important role as well. Getting creative with your strategy and taking risks are not comfortable ideas for everyone, but Wilson has picked up on some key characteristics that define a dealmaker.

Transferable Skills

Every year that Gary Wilson spent in the corporate world made him more miserable because he had to suppress his entrepreneurial mindset until he got out. When he broke away from that lifestyle, Wilson was finally in a position where he could pursue the unquenchable desire for financial freedom. The ability to look at things creatively and the desire to make them work are what set successful entrepreneurs apart, and it is a mindset that Wilson brings to every opportunity in his path.

Those skills define business leaders and entrepreneurs across a wide array of different industries, so there is an open door to real estate investment even if you aren’t going to put 100% of your time into it. The skills, attitudes, and talents needed to run a business are the same ones you need to succeed in real estate, and when you have both you gain an asset to borrow against to keep leveraging your business and vice versa.

A Cycle of Abundance

It is an amazing combination that creates a cycle of abundance. So, if you want to get into it, the resources you want to have are as follows: a tax accountant; a solid general contractor or contact in the construction/remodeling business; a good attorney; an investor-agent. The investor-agent is a key player in your venture because they can go beyond listing services to find the best deals that aren’t even published. Off-market deals are crucial in this space and Wilson’s entire brokerage company was based on that practice.

This industry has a learning curve and Wilson has made his fair share of mistakes, but if you are diligent and self-reliant you can avoid simple, costly screw-ups. It should not be a deterrent because the same risks apply in all facets of entrepreneurship. If you approach this business with a concrete strategy, mentorship, and a strong team, there is no telling what you will be able to accomplish with your current business and new ventures generating income simultaneously.

Listen to the interview with Gary Wilson on the Fueling Deals podcast to learn more about Gary and how you can apply your dealmaking skills in the real estate industry.

Corey Kupfer is an expert strategist, negotiator and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author and professional speaker who is passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.

If you want to find out how deal-ready you are, take the Deal- Ready Assessment today!