Best Practices for Sales Reps
Sales Prospecting 11.19.2021

Best Practices for Sales Reps

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This episode of Sunny Side Up is all about how to turn the successful sales reps fight so hard to achieve into long-term financial freedom and legacy wealth. Guest Matthew Buchalski has 15 years of experience with sales in both the financial/brokerage and high-tech sectors, but his wisdom extends beyond how to lead teams and close deals. He’s here to share best practices for sales reps and others interested in building wealth through smart investment planning and execution. The episode is full of great tips as well as resources to grow your knowledge base along with your financial bottom line. Join Host Asher Mathew for a turbo-charged conversation about what it means to pay yourself first, again and again.

About the Guest 

Matthew Buchalski (AKA Matt) is currently VP of Sales at Realpage. At the start of his career, he was a cold-caller at numerous stock brokerage firms in the late ’90s, spent time in credit card collections where he earned his first leadership role, then built a branch office of a small business equipment financing company from the ground up doing $35MM in small ticket transactions in 4 years. Matthew then moved into the tech space in 2010, working at T-Mobile then moving to CA Technologies, HPE, and ThoughtSpot, building and/or scaling sales teams.

Connect with Matthew Buchalski 

Key Takeaways 

  • Skills Matthew cultivated in the world of brokerage/financial sales (making hundreds of calls a day) transferred seamlessly to his work in tech sales.
  • For all the coaching sales reps get about confidently closing deals and moving forward fearlessly, when it comes to personally managing money many are risk-averse.
  • It’s all about compounding. When the windfall from sales wins shows up in your bank account, pay yourself first by investing early to reap accelerating rewards over time. 
  • Real estate is Matthew’s investment vehicle of choice because of its predictability (income and expenses) and the long-term housing shortage that will continue to spur growth.
  • Commission checks on the 30th are great, but what’s even better is receiving rent checks the next day! 
  • Many successful people are happy to answer questions and share how they’ve defined their path and succeeded.


“We as leaders should be doing a lot more to put our people on the path so that – once they become successful at their job – they can become successful in life. 

Highlights From the Episode

How did Matthew decide to focus on technology sales?

Initially working in financial/brokerage sales, in 2010 Matthew decided to make a transition into tech and has never looked back. He has worked with a range of companies – startups to Fortune 200 – and has had a great ride. But several years back Matthew decided to build a real estate investment business on the side, which has flourished. Skills he acquired making hundreds of calls a day early in his career have been useful in all other sales – and life – capacities.

What happens after you have sales success?

Financial freedom can’t occur without guidance. For all the sales grooming, training, and coaching, people very often aren’t literate when it comes to money management. People earning that seven-figure income? No one tells them what to do from there. The guidance stops and valuable seeds that should be planted for legacy wealth aren’t planted let alone growing. The earlier in your career that you figure out how to leverage earnings for long-term yield the wealthier you will be heading into midlife.

How does Matthew define financial freedom?

It means doing what you want when you want and without having to answer to anyone else. Anything else is numbered on spreadsheets and bank accounts. We need to help salespeople understand that investing in themselves early is a game-changer by the time they’re into the middle stages of their careers. You have to use the revenue from sales success and move it into multiple revenue streams that flow into your future. It all compounds and up until you hit 40 years old, there’s a tremendous tolerance for risk, mistakes, and recovery.

Why should people under 40 be tolerant of risk?

Mistakes are good. You don’t have to be an extremist, but there are things to be done (like rebalancing your 401k annually) that are simply about revisiting your priorities. How has your work, family, and life goal situation evolved? Are there certain things that you want to save for now that weren’t on the radar a year ago? Building wealth is an ongoing process.

What are Matthew’s No. 1 best practices when it comes to building financial freedom?

Pay yourself first. Save first, spend later. Keep that money rolling every month, investing every penny you don’t need to cover your basics. You don’t need to buy the flashy consumer item and will be glad you didn’t when you start accumulating wealth early on through multiple streams as your career proceeds and gains momentum. It’s a question of the alignment of values and the long-term view.

Which investment vehicle(s) does Matthew believe will generate the best ROI?

When it comes to building wealth, the investment platform of choice for Matthew is real estate. Why? Control. It provides a revenue stream with predictable expenses and net income which banks like to see. There’s a shortage of good housing options that Matthew doesn’t see abating in the next couple of years. Simple supply and demand make the equation pretty straightforward. Real estate is also something he’s passionate about – and that’s half the fun!

What are some of the ways to make money in real estate?

There are many ways to turn a profit with real estate. From an overall market and life cycle perspective, options include: fixing and flipping, wholesaling, long-term investing. But beware HGTV, which makes some of these options appear a lot easier than they are. Just be sure you know your bandwidth and have well-defined aspirations – and that they’re aligned. A lot can be achieved, but you’ve got to be prepared to burn a little midnight oil. 

What are some additional things that merit attention?

Tax planning is critical, particularly in a startup scenario but also when it comes to the timing of many other investments. Be astute when changing jobs. Most people just roll over 401k plans without realizing they can take their account into their own hands. When wealth managers call, pick their brains. They have valuable information to share. Pay attention to people who have accumulated wealth and start asking questions. How did you do it? Where does it start? What would you do if you were me?

Recommended Reading/Resources


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