It is a challenge for a family business to reach a second generation of ownership, much less a third. The percentage reaching a fourth generation is in the single digits. For the Bentley family, reaching a sixth generation after 170 years required hard work, a willingness to innovate and change, and some luck.
โAll it takes is one big lawsuit or one bad quote or a tough economic deal that puts companies under,โ said Todd Bentley, the sixth generation family owner, who turns 40 this year.
Today, the family operates Bentley World-Packaging Ltd. from a facility on North Port Washington Road in Milwaukee, helping manufacturers package and ship products around the word. The company has about 100 employees in Wisconsin and Baltimore, Maryland. For decades the Bentleys were in the construction industry, building iconic buildings from Alexander Mitchellโs mansion that would become the Wisconsin Club, to some of the largest churches in the state.
โThe construction guys, for four generations before me, they were tough,โ said Tom Bentley III, 71. โI mean, they had focus, they were determined โฆ they were just tenacious. They were going to maintain their construction business or die trying.โ
John Bentley, a Welsh immigrant who came to the United States at the age of 16, started the business in 1848. His son, Thomas R. Bentley, would eventually run the company and was joined in business by his four sons, including Thomas H. Bentley, who was part of the business for 70 years. Thomas Bentley Jr. started with the company in the 1940s and Tom Bentley III started in 1969. Todd Bentley, the current majority owner, got his start in 2003.
โI donโt think weโre as tough now,โ Tom said. โNow, weโre smart and we want to change and adapt and find new ways of doing business.โ
The Bentleys first got into the packaging business in the 1940s and Tom Bentley III would eventually launch the company as its own entity years later. It has continued to evolve from packaging, to helping companies with logistics, warehousing and packaging engineering. Building that business left the family with options when the Great Recession threatened the construction business in 2008.
โAll of the sudden, every prospect we had was going to sit on their hands for a year or two to see how this panned out and so there wasnโt a whole lot of choice, as every contractor either started to tighten their belt, let people go, start to save expenses, start to mothball some equipment,โ Tom said. โThatโs when I sat and had a long conversation with myself.โ
Tom ultimately decided to close the construction business to focus on packaging, and while he felt like there wasnโt much of a choice, it wasnโt an easy decision.

โI had nightmares of my grandfather getting out of his grave with a two-by-four and beating me because he didnโt want me to close the construction,โ Tom said. โThose images went through my mind, but when we had the packing company that was bigger, more profitable, had (better) margins, export was booming, I just said, โWhy would I fight this out and lose money probably for a year or two until the whole industry started to come back?โ Why would I do that? Just because of sentimental reasons or something like that? It wasnโt an easy choice โ Iโm not going to say it was โ but it seemed to be the only rational, logical choice.โ
Todd and Tom both say the family has been fortunate over the years to have relatively straightforward ownership structures focused on one person.
โThere was almost always one Bentley, from John to Thomas R. to Thomas H. to my dad to me. There werenโt uncles and sisters and aunts that were owners,โ Tom said. โThat was a pretty clean track that way. A lot of times these businesses go haywire because thereโs too many owners that own part of it or they have to sell it because they all want their money.โ
The transition in ownership from the fifth to sixth generation was complicated by Tomโs divorce from Toddโs mother, Sally, which left her owning 45 percent of the company. Todd, who had been buying shares in the business for about a decade, eventually bought his dadโs 45 percent stake last year using proceeds from the sale of the companyโs facilities in Pittsburgh, Cleveland and Cincinnati.
โYou donโt want exes involved that have large percentages of any family business,โ Tom said.
Todd acknowledged working through the complexities of ownership made the transition difficult at times, but said the intergenerational dynamics of managing the business added to the challenge. He said many family businesses might falter if the older generation is not willing to hand over control.
โItโs actually very rare that that works well,โ Todd said. โEven in our situation, I wouldnโt say it worked well. It worked, we got through it, but it wasnโt pretty.โ
A parent-child relationship is not the same as the relationship with an outside hire, which Todd noted further complicates the dynamics as one generationโs influence rises while the otherโs falls.
โI think itโs hard between the generations to fully support that next generation, at some point to your detriment,โ he said.
Having built the packaging business and hired many of the key employees, Tom said he recognized he needed to step aside to allow Todd to be in charge.
โIf I was coming to a meeting, often people I hired were looking to me for a stamp of approval on things and I had to get out of here just for that reason alone,โ Tom said.
Todd said the dynamics will probably be similar with his children โ two daughters and one son โ if they take an interest in the business. At this point, however, all three are too young for succession planning. They come to the office with their dad occasionally on weekends and might have an opportunity to start working in the future.
โI think theyโll do what you and I both did,โ Tom said to Todd, โwhich is get their feet wet at some point while theyโre in school and start to decide a little bit whether this sounds like fun or doesnโt.โ
Todd is sure of one thing: the next generation will have to earn the right to take over the business.
โIf weโre in a position to pass it to the seventh generation, whoever would end up in the seventh generation taking it needs to deserve to own it,โ he said. โTheyโre not going to get there because they happen to be a son or daughter of mine. They have to get there because they are better and more capable and willing to work harder than anyone else.โ
He said when the time comes, it will be important to have a plan with clear hurdles and expectations for the next generation to overcome. For now, the focus is on positioning the business itself for the future.
โThe focus right now is to really strengthen and grow the business and hopefully Iโve got a kid who has the ability and desire to come in and someday run it,โ Todd said.