IT guy here that is currently just a system in at an insurance company doing mainly Citrix and VMware support.
I did 2 years at 3 MSPs in the central Arkansas area. Here's a couple points taken away.
The most successful company had 3 separate companies, IT, printers leases and low voltage cabling. The low voltage cabling was probably the most consistently profitable. Those guys were always back logged on jobs. Took pride in their work and posted bundles and bundles of cables always /r/cableporn worthy. Leased printers were more of hook to get into the IT consulting for the business. Businesses always price out a cheaper printer lease. Or if they sold IT services / website. They'd also offer the printer lease.
One of the more successful smaller ones was this guy who operated in this Executive Networking Group. It was a group of about 30 business owners that basically had a pact go always recommend one another. There was only one business from each field allowed in. Rentalcar, flowershop, accounting, dentist, constuction/roofing, leasing company, staffing company. This networking group was ran as its own business and referrals within the group were crazy! We'd always get calls about "Ted told me to call" usually it started with a business owner recommending a business owner to us to fix an ipad. Then we'd have his IT contract next week.
The smallest of the 3 MSPs. It was 3 Web developers 1 owner + 2 full time staff. Then me. The website guys kept fielding questions about general tech support and they decided to wrap it into a package and sale it. They Hired Me to Do this bitch work. In my downtime i would target local businesses similar to what we already had. We had one optometrist shop with a couple locations. So one day during down time I'd go through the yellow pages and call every optometrist. My line was something along the lines of "hi I'm jhulbe calling from hyperglobalmeganet. We do IT work in the xylophone area. I was wondering if I had time to drop by and give the business owner or office manager a card. So in the event you're ever in a bad place with computer problems you have a back"
I'd try to schedule a time to drop by with a name of who too meet. Usually I'd scope.out the office and bring coffee that morning or bagles. Then bullshit for a little while. Ask them if you can put them in the kitchen or breakroom for them.
basically anything to get the person in charge talking to you. Another approach on the initial call would be to say "I'm just a local business owner looking to network with other business owners."
I'd never really sale. Just introduce who I am, see if I could figure out who they used and if they were happy. Then Leave my contact. I eventually left that job because it became more sales Than tech. I'd say i had about 15% close rate.
Once I got through all the offices in one field I'd go on to say vets, or accounting firms, plant businesses. If I could figure out their accounting software in conversation I'd casually drop something like "oh have you seen the new reporting in great plains 55, we just upgraded a competitor to that and it's nice" r oh.. quick books. Do you have that configured so multiple people can access it at once? If I found out anything I had a list of pain points I'd poke at to get them to either call me back or talk to me about it right there. Phone systems, chat programs, employee logging, digital time tracking... I'd start scoping the bitch out the second I went into the office.
...man maybe I'm in the wrong field.