Lesson #380: What Happens To Your Business If You Die? Legacy Planning is Critical.

I was recently engaged by the estate of a founder to assist in finding a new owner for their business after the founder died.  There were a lot of valuable business lessons that came out of this process that I wanted to share with you.  Not for your estate survivors after you die, but instead for you before you die, so you don’t repeat the same mistakes of this other entrepreneur that failed to properly lay out a clear legacy plan in the event of his death, leaving the survivors scrambling looking for answers in the wake of his death.

The Business and Situation

The business here was a solo-owner charitable foundation that runs a big annual event, an event that was run by the founder for decades.  The founder died with no clear plan for what do with his business in the event of his death, especially with nobody in his family wanting to pick up the reins.  But everyone associated with the event wanted the event to survive for years to come, especially to honor the legacy of the founder.  The problem was we couldn’t get into the head of the founder to ask him who he would have liked to take over for him.  Instead, we had to come up with candidates on our own.  And that left a big void for us to fill.

Step One:  Search for Breadcrumbs Left by the Founder to Help Guide Us

The founder had considered putting a transition plan in place in the past, and we were fortunate to find a few files in his office that referenced those specific partners.  He even went so far as having detailed merger discussions with two of them, the notes and draft agreement left behind in the files.  But how do we interpret that?  Yes, they are good candidates because the founder thought they were good candidates in the past?  Or, no, they are not good candidates because they never got to the finish line for some unknown reason?  We decided to pursue them, to see if there was any interest in rekindling those old discussions.

Step Two:  Speak to the Staff and Current Board of the Business For Their Thoughts

The surviving staff had been associated with this business for years and did offer up several specific suggestions of potential companies to reach out to, to take over the event.  But the staff were more execution-level in their approach and thinking, and I was looking for more of a strategic-level list of companies where the missions of the two businesses were perfectly in alignment with each other, to increase the odds of long-term survival of the event.

The board was also helpful, in that they presented themselves as a candidate to take over the event, given their decades of history there.  But that presented a couple problems.  Their recommendation was biased for their own personal interests, and it is one thing to be a board advisor, and another thing to be the actual event operator, and they didn’t really have those needed operational, marketing and fundraising skills.  There was also the issue of the event having struggled for the last couple years to grow its audience back to historical heights, and the fear of handing the event off to the same team that oversaw such historical declines.

Worth adding, I was curious why only some of the board members reached out to me to express their views, and I hadn’t heard from the others.  So, I called a few of them to seek their input, figuring they did not have a “horse in the race” and would give me a candid opinion.  Those were very telling conversations; the board members were not in alignment with each other, with one half of the board not really desiring the other half of the board to take over, to keep their going forward involvement.  I wasn’t expecting that, but it certainly helped directionally find a partner that would be embraced by most all.  And in this case, it wouldn’t be the fractured existing board. 

Step Three:  Figure Out Your Exact Needs and Outreach to New Partners That Fill Those Needs

We came up with a scorecard of everything we wanted to find in a new partner. Things like strategic fit, financial resources, event production experience, event marketing experience, reputation, interest in preserving the legacy of the founder, personality fit, vision, etc.  Strategic fit was the most important and we came up with a short list of organizations that served this same target market and reached out to each of them, interviewing each of the interested parties for the criteria above, and ultimately selecting a winner that “checked all the boxes” to move forward with the transition.

Step Four:  Prepare for a Lot of Bruised Feelings

In this project, we had five interested parties, but only one could win.  And one of those parties, the current board, felt they were “entitled” to win this event given their decades of history with it.  But it was clear for many reasons they lacked the needed skills to be successful in not only running the historical event, but growing it into something bigger and better than it had ever been in the past, to truly honor the founder’s legacy.  When many of these board members learned they did not win this process, the decided to entirely disengage with the event.  Which is really sad.  As that meant it really wasn’t about the event, or the cause, or the founder’s legacy that was important to them; it was simply their personal ambitions which was driving them.  That confirmed we made the right decision.

The other issue to navigate through was all the various surviving family members had differing opinions of how the process should be run and who should ultimately win the event.  And there was no way to make everyone happy, which bruised a lot of feelings that their opinions were not being listened to.  But without the founder making his intentions clear, and “lots of cooks in the kitchen” in the wake of his death, the project was ripe to leave people feeling discontent.

Step Five:  Hug All Legacy Partners and Make Them Still Feel Loved to Embrace the New Partner

In addition to making room for all the old board members to stay engaged in leadership roles with the new event owner, there were lots of event sponsors, vendors and other partners that needed to be communicated with and embraced to keep them involved in the future.  In this case, the event was so tied to the founder, that there was a risk of many of the historical partners not continuing their involvement going forward.  But with the right communication strategy, vision and outreach plan, we were successful in getting most historical partners to continue their involvement with the new ownership.  But in the absence of the founder giving clear direction here, to ensure his legacy desires were communicated to all ahead of the time of his death, I think we did a good job of filling that void.

The Moral of the Story

The survivors of the founder should have never been in this situation in the first place, having to “guess” what the founder would have preferred to happen to his business in the event of his death.  It is very important you document your desired transition plan for your business somewhere.  It would have been so much easier for the survivors to simply shut down the business and move on with the rest of their lives.  But in honor of the founder’s legacy, they put in the work to make a smooth transition happen. Hopefully, the founder is happy with the selected outcome, but I guess we will never know for sure.  Don’t put your own survivors in this same situation when you die.

For future posts, follow me on Twitter at: @georgedeeb.

[VIDEO] Don't Chase Short-Term Revenues at Expense of Long-Term Success

I was recently interviewed by ASBN, an online "television network" serving the small business community, about potential pitfalls entrepreneurs fall into when chasing short-term revenues.  This video will help you learn which types of revenues/clients to avoid so it doesn't negatively impact your business.  As you will learn, all revenues are not the same shade of green.  I thought this video turned out great, and I wanted to share it with all of you. I hope you like it!!

The embedded video player didn't give me the option to change the size of this video.  But, if you want to see a bigger version, simply click the expand size button in the player above.

Thanks again to Jim Fitzpatrick and the ASBN team for having me on the show.  I look forward to our next interview together.

For future posts, please follow me on Twitter at: @georgedeeb.

Stick to Your Business Plan--Making Sacrifices Can Lead to Negative Consequences

When you are an entrepreneur, you want nothing more than to see ‘your baby’ grow up into a successful business, especially with all the headwinds that are sure to come your way. That often means that those same entrepreneurs are willing to make sacrifices, veering off on tangents away from their stated business plan. I am not talking about business pivots in a new direction, which would ultimately require an update to the business plan. I am talking about keeping the same business plan, but making exceptions to the stated goals, just to make some progress with the business. That is when you can get into a lot of trouble. This article will help you learn how to avoid getting trapped in those rabbit holes.

Read the rest of this article in Entrepreneur, which I guest authored this week.

For future posts, please follow me on Twitter at: @georgedeeb.

Lesson #379: Business Lessons from Curt Cignetti and the Indiana Hoosiers

By now, we have all learned there is a “new sheriff” in the world of college football.  No, not my beloved alma mater, Michigan.  Not other “blue bloods” like Alabama, Georgia, Texas or Ohio State.  It is the team that up until two years ago had more losses than any other program in history: the Indiana Hoosiers.  In just two years since the hiring of their head coach, Curt Cignetti, they sit alone atop college football as the 16-0 national champion this year, including three wins over teams ranked in the top five (tripling such top-five ranked wins in their entire 138-year history).  How was this even possible?  This worst-to-first story will go down as one of the greatest stories in college football history. Let’s dissect this further, as there are a lot of valuable business lessons to be gleaned here for your businesses.

To summarize how this amazing turnaround happened for Indiana, it came down to the following things: (i) market conditions changed to their benefit; (ii) ownership embraced the desire to win at football; (iii) they hired a smart leader; (iv) the leader had a clear vision of the type of team he wanted to recruit; and (v) they all bought into the vision, believing the impossible was actually possible, and put in the hard work to make it happen.  Let’s dig into each of these points.

Market Conditions Changed in College Football

Two things happened in college football in the last couple years that forever changed the sport: (i) the NCAA allowed players to get paid, through name-image-and-likeness deals; and (ii) the NCAA allowed players to freely transfer between teams through the transfer portal.  Paying the players meant that the schools with large alumni bases (Indiana is the largest) and wealthy alumni (like Mark Cuban at Indiana) could amass large sums of money, to put them on a more even footing with the historical “blue blood” programs.  And the transfer portal enabled players to move between teams if they didn’t feel they were getting enough playing time or didn’t like their coaches, which meant the historically second and third string players at the “blue blood” programs were now starting at the other schools that were willing to pay for their services.  These changes became the big equalizer in college football.

I don’t like a lot of these changes, as it feels like the Wild West right now with limited guard rails being imposed by the NCAA.  But these changes were earth shattering for the sport.  Instead of a season ending with 4-to-5 teams that were capable of winning a playoff and the championship, now there were 15-20 teams that were good enough to go on a run and win a championship.  This created more parity than ever before.

As we apply this to our businesses, think of what artificial intelligence is doing in the workplace; it is the great equalizer putting both big companies and small startups on a more equal footing.  Your startup’s market conditions have materially changed in the last couple years; how are you going to capitalize on that?

Ownership Embraced The Desire to Win

Indiana never really was considered a “football school”.  On the other hand, with their success under coaches like Bobby Knight and players like Isiah Thomas and Steve Alford, they were always considered a “basketball school”.  But basketball isn’t where the lion’s share of athletic revenues are generated—they come from football.  And Indiana was never going to truly maximize their athletic revenues until they set a clear goal of being successful in football.  University President, Pamela Whitten, and Athletic Director, Scott Dolson, made that a priority, and began to invest accordingly.

What is the “North Star” vision for your business, and are you making the appropriate investments to enable you to hit that target?  If not, you will never get there.

They Hired a Smart Leader

Not many college football fans had heard of Curt Cignetti prior to his time at Indiana.  His name was never mentioned in the list of college football’s great coaches, like Kirby Smart at Georgia, Ryan Day at Ohio State or Dabo Sweeney at Clemson.  But when Indiana’s leadership started to research him, it was clear he was a winner wherever he went. 

In 2009, he was on Nick Saban’s coaching staff at Alabama that won a national championship (and who better to learn from than college football’s greatest coach of all time).  Between 2011-16, he turned around a struggling IUP program into a perennial conference champion.  In 2019, he lead James Madison to the FCS (Division II) national championship.  When Curt Cignetti famously told the media, “I win.  Google me!”, he wasn’t kidding.

The business lesson here is to hire smartly.  It isn’t always the person with the biggest brand logos on their resume, or the most attention, that will be the best hires.  Do your homework, peel back the layers of the onion, and you may find your own “diamond in the rough”.

They Recruited The Right Type of Players

Most college football recruiting classes are ranked in order of how many “5-Star” high school recruits a team has.  Indiana didn’t have a single 5-Star recruit on their roster that won the national championship.  Cignetti did three smart things in this regard: (i) he brought around 15 players with him when he moved from James Madison to Indiana (experienced players that had won a national championship and who could lay a good foundation for instilling that same mindset with his new team at Indiana); (ii) he biased the transfer portal over high school recruiting (take a proven winner at the college level than an unproven recruit from high school); and (iii) he looked for players that had the same “chip on their shoulders” that he did (the under-loved, under-recruited, under-appreciated players that wanted to prove themselves, like quarterback Fernando Mendoza that went on to win the Heisman Trophy and beat the team in his home town (Miami) that didn’t think he was good enough to even walk-on to their team).  What a recipe for success this turned out to be!

The same holds true for your business—people really matter.  Find the experienced staff member, perhaps from your competitors, wanting to prove they can succeed at the next level.

They All Bought Into the Vision and Put In The Work

Bo Schembechler, the famous Michigan football coach once said, “What the mind can conceive and believe, the mind can achieve. And those who stay, will be champions.”  Curt Cignetti must have said the same thing to his team.  If you think of Indiana as all-time biggest losers, that is where we will stay.  But if you actually believe you are on an equal footing with the greats like Ohio State, Alabama, Oregon and Miami, you can actually beat them (which they did in four consecutive games).  But more than believing, they had to put in the work, winning in the weight room, practices, coaching sessions, film watching and game planning, as well.    That “chip on their shoulder” was particularly helpful here to get them to put in that needed work.  Big picture: winning is a mindset and to get there, it requires discipline, which Indiana had in spades.

Are you clearly communicating your vision to your staff?  Have they bought into that vision?  Are they putting in the hard work which will be required to win (e.g., gain market share and exceed  your goals)?  If not, back to the drawing board, as without that vision, a clear strategy and communication, religious management and hard work, you will never get there.

Closing Thoughts

When Indiana went 11-2 in 2024, Cignetti’s first year, I thought it was a fluke, catching better teams by surprise.  But when Indiana was the first team ever to go 16-0 to win the national championship in 2025, beating top-ranked teams by large margins of victory, I knew Indiana was no longer a “basketball school” and their football success was here to stay.  Which is bad news for my Michigan Wolverines and everyone else in the Big Ten. 

In the last two years, Northwestern has now passed Indiana as the team with the most all-time losses in college football.  Maybe Dave Braun and his coaching staff will be the next team to achieve the “impossible”, winning a national championship in the coming years.  Indiana has certainly given them and ever other team in football that winning playbook, which everyone is trying to copy in hopes of “catching lightning in the bottle” for their programs.  Expect to see more “historical underdogs” hoisting the championship trophy in years to come, thanks to Indiana and Curt Cignetti paving the way, proving what is actually possible with a well-conceived vision, strategy, team and execution.  Which “blue blood” will your business beat for your “national championship”?

    

For future posts, please follow me on Twitter at: @georgedeeb.

[VIDEO] Is Entrepreneurship Learned or Wired Into Your DNA?

I was recently interviewed by ASBN, an online "television network" serving the small business community, about whether entrepreneurship can be learned or if it is wired into a person's DNA.  This video will help you learn the 7 skillsets needed to be a successful entrepreneur, and whether they fall into the learned or DNA category.  I thought this video turned out great, and I wanted to share it with all of you to see if you have what it takes to be a successful entrepreneur. I hope you like it!!

The embedded video player didn't give me the option to change the size of this video.  But, if you want to see a bigger version, simply click the expand size button in the player above.

Thanks again to Jim Fitzpatrick and the ASBN team for having me on the show.  I look forward to our next interview together.

For future posts, please follow me on Twitter at: @georgedeeb.

Lesson #378: Artificial Intelligence Can Do Everything Now--Good News For Owners, Bad News for Staff

 Artificial intelligence (AI) has been more than a buzzword for the last couple years; it is literally taking over every single aspect of how businesses are run.  Big corporations have even started hiring Chief Artificial Intelligence Officers to ensure their organizations are getting the most out of AI tools, largely to replace slow/expensive human-driven tasks with fast/inexpensive technology-driven tasks.  The applications are literally endless, but this post should help inspire you to rethink everything you are doing in your business, as there is probably a technology out there that can do it faster and cheaper.

I did a little researching on Google to see what AI tools I could stumble upon, and I was amazed at the breadth and depth of AI tools I found:

Need a business plan?

Need market research?

Need competitor analysis?

Need products designed?

Need marketing help?

Need customer service support?

Need technology coded?

Need financial reporting?

Need fund raising?

Need to recruit staff?

Great, there are now AI tools out there that can quickly and easily do all of these tasks.  Yes, you can get a lot of these same topics addressed from the main AI engines like ChatGPT, Claude and Google, but the businesses linked about are mastering their craft in each of these specific verticals.  So, as we are all experimenting with these main AI engines, we should also be experimenting with some of these niche solution providers we have never heard of before, as maybe they have a better “mousetrap” (at least for now).

Why do I share this?  For three reasons.  Firstly, an “old timer” like myself (aged 56) would have done what I normally would have done for these topics: hire people or consultants that produce the work product needed.  Because that is how I have always done it.  I didn’t even know there were other technology driven options out there that could help me move faster and cheaper.  And I am guessing there are a lot of other people out there that would have done the same thing.  So, I encourage you to take a pause, see what technology options are available to you and see if they can help you save time and money versus the “old ways” of doing business.

Secondly, if these new technologies prove effective, it is going to dramatically decrease the amount of capital that will be required to get new startup businesses launched and operating in the market.  Which means the speed at which your business faces new competition will be much faster.  So, you no longer have the benefit of “resting on your laurels” or coasting based on your past successes.  It won’t take long for some smart AI coder to launch a better product, making your business obsolete.  So, you need to protect your turf and go on the offensive:  figure out how AI can help you with your product development roadmap and innovation efforts.  If you don’t, someone else will!

Thirdly, all human workers out there should be “shaking in their boots”, in terms of thinking about their job security.  Yes, companies like Amazon or Google say AI will help reduce their future hiring needs, letting them grow more efficiently while keeping all of their current staff.  But lets not fool ourselves; companies are driven by their shareholders that are seeking higher valuations, typically from higher profits.  And what is the best way to increase profits?  Replace a $60,000 a year salaried person with a near-free technology!  Yes, I am talking to all you graphic designers, technology developers and customer service agents!

While that may sound great for that specific company’s bottom line, if all companies out there are employing this same logic, this could mean massive layoffs in the years to come, with no replacement jobs that will enable them a “soft landing”.  It wouldn’t surprise me if a majority of Americans were living on welfare in the next decade or two, which is a pretty bleak forecast.  The stock market may do great, with all the accelerating corporate profits as technologies replace people.  But the average American and their consumer spending power is going to be materially impacted for the worse.

Yes, all of these new technologies are very cool.  Who doesn’t want to move faster and cheaper on their growth plans?  But when you think about the long term implications of these AI technology advancements, it doesn’t paint a very rosy picture for the future of most average Americans.  So, if you are worried about getting potentially disintermediated by technology (which should be most of you!), start putting your “defense plans” in place now.  Start training yourself up with new skills that won’t get cut by profit-hungry management teams.  Who knows, maybe you can use the AI technologies to your advantage, in launching the next really great startup that everyone will be using.

It will be very interesting to see how this all shakes out in the coming years.  At a minimum,  you all need to be learning how AI technologies can help your businesses and or your specific roles.  If not, you may not have a profitable business or a defendable job for much longer.  Sorry to be “doom and gloom” here, just calling it like I see it.

For future posts, please follow me on Twitter at: @georgedeeb.