October 22, 2025
When I sold Future POS back in 2017, I had no idea that the entire industry was going to go to hell in a handbasket. Yes, private equity was buying up POS ISVs in what amounted to a game of “musical chairs”, where at each turn the next best chair got removed from the floor. I thought (perhaps naively) that PE would buy some companies, invest in some cloud tools that each product could integrate with, and give the customer some value for moving their credit card processing to the PE POS company. PE POS would build their new POS product slowly and over time replace those companies as their products got mature and robust enough to do so without major hardship to the customer.
Nothing could be further from what actually happened. Micros was being run into the ground by Oracle due to lack of domain expertise and little regard for smaller merchants. Aloha, the de facto number 2 product for decades, became an ancient artifact due to lack of any meaningful investment. The table was set for the products that Shift 4 purchased to pick up significant market share with a little bit of investment in those products. All they needed was to add some Cloud capabilities and they could have easily kept Toast at bey for several years while SkyTab was being built and tested thoroughly.
Nope, that’s not how it went. Shift 4 purchased Positouch, Restaurant Manager, Future POS, Focus POS, and Revel; so far so good. They could have created some “deal sweetener” technology and converted those merchants to Shift 4’s processing by giving the customer some value to do so. Instead, they sunsetted all of those products far sooner than they should have, and tried to cram SkyTab down everyone’s throat before it was ready for primetime. After purchasing products that account for probably 150K merchants or more, they essentially strong armed those customers right into Toast’s grubby hands. If I was running Toast, I would send Shift 4 a Christmas card every year to thank them for the awesome gift. They also had the effect of alienating many of the VARs, pushing them to Spot On or even worse; “payments agnostic” POS.
So where are we now? There has never been such a stark contrast between POS ISVs, and they basically fall into two camps: Private Equity POS, which is going to try to squeeze every penny out of the merchants to pay dividends to their shareholders. Zero concern if they hurt or even run those merchants out of business. The other camp is legacy/payments agnostic POS. Ancient technology and zero payments strategy, making them so irrelevant that Shift 4 wouldn’t touch them. Their only claim to fame is “payments agnostic”, which means they have no money to ever reinvent their products. Just an evolutionary dead end!
So, what’s a VAR to do? Toast doesn’t want you, the industry has seen what Shift 4 has in store for the VAR, and Spot On is on the auction block because they’ve blown over 1 BILLION dollars to take a mediocre product and give it a face lift. After that you get into Windows products that are 30-year-old dinosaurs with no intention of creating a modern version of their product. Hardly something you should use as the foundation for a great VAR.
Enter Round 2 POS. So, after I sold Future POS, I didn’t just sit by the pool sipping umbrella drinks. I went to work vetting technology. I started with a used Epson TM-T88 printer that I purchased on Ebay and spent a couple months making it do things I never had the time to figure out in the Future POS days, namely how to store logos in the NV memory using code that I wrote (an industry first). Next, I tested 4 different databases; I started with MySQL, then tried MariaDB and Mongo, and ended up on PostGreSQL. After that I focused on which Operating System would make sense for the modern day; Windows was too bloated and clunky, iOS is an evolutionary dead end for POS and Android is subject to change by Google with zero warning. The only real option that wasn’t fatally flawed was Linux. Having decided that, I installed probably 50 different Linux distros on an old POS all-in-one to see how they performed. For the sake of time, I won’t go into this selection process, but needless to say it was very thorough.
Because the payments industry has forever been merged with POS, we approached that side of the business with the goal of giving the VAR the tools they need to compete in the modern day. We created the Round 2 CRM, which is integral to not just lead management, but also does Statement Analysis using A.I., Electronic Merchant Application Submission (13 minute turnaround), and gives full transparency into your CC portfolio so there can be no “fuzzy math”. Round 2 CRM also fully integrates with Round 2 POS, and gives the VAR the tools they need to manage their entire fleet of Round 2 POS systems in the field. It does way more than what I’ve mentioned, but again, for the sake of time, contact me if you want to learn more. The most important takeaway: YOU, the VAR, control the credit card pricing for YOUR customers. We don’t nickel and dime your customers when you’re not looking; you’re fully in control of what they pay and their rates don’t go up unless you, their VAR, decides to raise them.
So why did I do this? I’ve been asked that question dozens of times: “You could be on the beach sipping umbrella drinks. Why the hell did you ever want to come back to this?” I guess the answer to that question has evolved over time. In the beginning, I just had a “tech itch” to scratch. I love technology and finding ways to leverage it to make people’s lives better. But then Covid hit. I watched my friends in the restaurant industry struggle with insane social distancing edicts, and also watched them get fleeced by all of the food ordering apps. My restaurant people were getting squeezed from all directions, and I wanted to help. Then I saw my friends in the VAR community have the rug pulled out from under them because the products they had sold for decades were suddenly shut down. What started as a fun tech project evolved into a way to pay my good fortune forward and help the people I care about.
How does a VAR know I won’t sell again? A fair question, considering I never intended to sell Future POS. Simply put, the offer was way too generous and as a businessman it was a great opportunity to “take some chips off the table”. It also provided me with the sizeable war chest that I leveraged to create Round 2 POS and Round 2 CRM. I’ve certainly second guessed the decision to sell Future POS over the years, but the fact of the matter is that I would be one of those legacy POS companies peddling a long-in-the-tooth Windows product if I hadn’t taken the Shift 4 offer. Now I have the most modern and innovative platform in the POS marketplace. I’ve also committed to making Round 2 POS an ESOP, so that it can never be purchased by another payments company. So, when that day comes, my employees will get quarterly profit-sharing bonuses BUT, those bonuses will be throttled by the results of surveys we will send out to our customers and VARs. My goal is to create an ecosystem where everyone’s interests are aligned; our customers and the VARs will have the “power of the purse” over my staff, so if my people don’t take care of the customers and VARs, they’ll feel it in their bonuses. As a VAR or POS customer, you can’t ask for much more than that!
In summary, if you’re a VAR who doesn’t want Payments Bro POS or products that are older than your children, Round 2 POS is pretty much you’re only option. Please reach out to us so we can show you firsthand what makes Round 2 POS and Round 2 CRM the only sensible choice for a VAR who wants to be here in 10 or 20 or even 50 years.
