Samuel Dempsey

⚠️Cleveland SMB/ETA Community⚠️ The time is NOW! GET READY FORRRR….. The Cleveland SMB Meetup!🚨🚨🚨 Come by and meet some local Cleveland business owners and searcher friends over some casual drinks, have fun! All hosted by yours truly at Masthead Brewing Company on March 26th at 5pm This will be a glorious event Please RSVP if you can make it (link below) Tagging 1 or 2 of my Cleveland peeps: @kelceylehrich @JScheeff @WilsonCompanies @BrandonNiro @oneill_patrick @montinifrank @SD3mps @seanmcginnis @dnabiznate @ATMNewsome @AlexanderGreezy @SMB_Merch @tucker_SMB @mattclekennedy @paulroetzer @tpietrocola @AaronFaz @alexforbes__ @wanderinmoose @PeytonZachrich @tylerjdunagin @MichaelMurray3d @Brendan_Andersn @HoldCoConf (yes, you are invited Kristen!) @erisaohio @BradyR34 @Whiteboardfin @nathan_e_hill @BednarikMatt @MikeForan21 @jjtejkl @BGPaul @drkinger @tucker_SMB @JacobWBailey @yaswanthpreddy @tjdowhan @steveostick @ethanard @mrcottrill @SBAChadF @AlexJoyceSMB

I have NO IDEA whether I am a good business person or not. I have NOT been through any Great Financial Crisis. I don’t know what it’s like. What I DO know is that I will be road tripping through these cities over the next 2 months, throwing free SMB/ETA meetups. Cleveland Pittsburgh DC Baltimore Philadelphia New York Boston Syracuse Buffalo Toronto Detroit Chicago We will call this trip… “The Rand Run” The Rand Run prioritizes a fun night of conversations, deep connection, and mutual respect instead of the opposite of those things. If you want to have drinks and meet new friends in your local town, I will help make that happen. DM me if you’re in these cities, so I can build a list and get a headcount. And please RT if you think this is awesome

I interview SMB CEOs for a living. Their stories can’t be shared publicly. But, I can act as a surrogate. Here are 6 realities of buying businesses that you will never hear about on Twitter… Big a** thread: 1. Recession fears: real and perceived… Some folks are going through it right now. Their businesses are slowing down, cash is running low after a slow winter, they’re cutting their salaries to get by and trying to retain talent. But you can only burn so much cash until it runs out. Other folks have started to see signs of a recession but haven’t been hit by it yet. They’re figuring out how to bolt down the hatches, build cash, and make safer moves (while still buying more companies). Most owners I talk to think we will see a downturn for the next 1-2 years. No one has a good guess on how significant it will be. 2. Deal flow is different if you have already acquired a business. Despite these signs of a recession, it seems anyone who currently owns a business has solid deal flow, whether it’s sourced proprietary or organic inbound. My guess is that, a) sellers want to find as much safety as possible with their buyer. Finding someone local who’s already acquired in their market is the best bet. b) organic deal flow = social proof. When a local owner hears about an acquisition near them, it builds trust with whoever the acquirer is (so long as no bad news of the new owner spreads to them). 3. Sellers can be a PITA. From the acquirers I talk to, It seems like a 50/50 shot whether the sellers are good to work with or not. Overall, it’s a hard transition for the seller, they’ve been an owner for 20-30 years, they’re not used to being an employee. On top of that, good acquirers will change the business, grow it, and make employees happier. It can be difficult for an owner to see someone else run their business better than them, especially quickly. I think the rule of thumb for an owner to be out of the business after 3 months still applies in most cases. 4. Employees can be a PITA. There’s a lot to be said here, but I’ll say 2 things a) Managing employees is just a hard job. Some employees respond to a hardass boss, some need a shoulder to cry on. Some are resistant to change, some need it. Some require consistent motivation and attention, others don’t want to see those employees getting special treatment. The number of times I’ve heard a business owner say they “feel like a therapist most of the time” is uncanny. You don’t learn about this stuff in business school. b) Some employees suck I once asked a business owner what the most difficult part was about his new acquisition, He said: “I wouldn’t say there is one crazy story. But issues that I have been dealing with.” - Time fraud with hours - Employees quitting the same day - Employees having relationships with each other causing drama - Employee stole toys for totes - Employees stealing customers away, then stealing from those customers If you’re buying an SMB, the likelihood of you having to deal with issues like this is almost guaranteed given enough time IMO. 5. Exhaustion/Depression Running businesses is exhausting. Think about this… - You’re a business owner - probably dealing with one of those issues listed above - trying to do your job - trying to interview candidates for a new tech or management role - and in the same day an employee’s truck *literally* blows up - and you have the largest sales meeting of the business’s history in 45 minutes. (This is a true story) This isn’t every day in SMB life, but you shouldn’t be surprised if this happens every week for months on end. 6. Loneliness Think about the amount of stress the owner had in the story above. Who can he share that with who would actually understand and relate to that pressure? He can’t tell his employees. He can tell his wife, but she can’t actually relate. He can tell his friends, but they’ve never been through the same thing. They can’t actually help. Even if he could, how could he admit any personal failures he had in those moments? How could he get feedback to deal with this situation better the next time? Most business owners don’t have people in their lives they can talk to about these things. I’m building SMB peer groups to solve this problem. if you’re a business owner who wants to talk regularly with 5-6 peers in your industry… DM me @RandBusiness (if you liked this thread, please RT to share it)