Solve Rich People’s Problems: The Fastest Path to Capital, Cashflow, and Opportunity

Sir Darren Jacklin (00:00)
Because the fastest path to cash is solving rich people’s problems. Because they will pay you for speed and execution. So what you want to do is if you want to make money quickly, you need access to capital, hang around rich people. Why? Because rich people are always looking to deploy capital, but they’re always looking to get things done and produce measurable results.

Michelle Kesil (01:49)
Hey everybody, welcome to the Real Estate Pros podcast. I’m your host, Michelle Kesil. Today I’m joined by someone I’m looking forward to chatting with, Sir Darren Jacklin, who is a real estate investor across the North America, US and Canada, as well as the owner of Smashing Numbers, which does bookkeeping, taxes and account services across North America for investors. So excited to have you here today.

Sir Darren Jacklin (02:18)
I’m grateful to be here, Michelle.

Michelle Kesil (02:20)
Great, let’s dive in. So first off, for those not familiar with you and your world, can you share what your main focus is?

Sir Darren Jacklin (02:28)
So my focus right now is solving a big problem across North America of an aging population of men and women that are baby boomers. And they’re transitioning right now into their sunset years towards retirement. And we’re seeing a lot of small business owners who’ve been around for decades running small businesses. So right now I’m focused on doing what we call a roll up strategy with smashing numbers. So a few years back we identified a big problem with an aging population of baby boomers. So right now we’ve completed multiple acquisition targets over the last few years.

a bookkeeping, accounting, tax planning, and payroll services companies across the United States of America. Now we’re into transitioning to Canada. So not only do we come in and make a financial offer once we go through the discovery process and due diligence of these ⁓ bookkeeping, accounting, tax planning, and payroll services companies, we buy their book of business, we transition their employees, but we also look at the real estate assets as well. So we have two separate companies. We have Smashing Numbers, which takes care of people’s bookkeeping, accounting, tax planning, and payroll services, but we also have a real estate side where we buy the physical bricks and mortar buildings.

And we look at producing positive cashflow on there. So the thing is right now is we’re growing and scaling, smashing numbers to an international company, to a multi eight figure company down the road. We do a few million dollars a year in revenue now. And yeah, we’re having a lot of fun. And one of the things is that people have a lot of fear and there’s a lot of speculation about artificial intelligence. But a lot of people right now out there in the marketplace are sensitive to confidential information going, being uploaded to a like a chat, GDP or a plot or something like that, because you become vulnerable.

and exposed to potential risks and liabilities when you let go of confidential sensitive information to some source that you have no ownership or control over.

Michelle Kesil (04:04)
Yeah, absolutely. And what made you create smashing numbers?

Sir Darren Jacklin (04:10)
Great question. So I served for a decade on a public board of directors called EXP Realty, EXP World Holdings. I served on that company, which at the time a few years ago was the fastest growing residential real estate company in the world. It’s a NASDAQ listed company. AGNT is the symbol on NASDAQ. So I joined it when it was a startup residential real estate company with only a few hundred people in the company and helped grow it over a decade to a multi-billion dollar company in over 26 countries around the world and billions of dollars in assets.

And so what happened was I realized a pattern of a lot of top producing commission sales real estate agents across North America internationally. A lot of these men and women are very good at selling homes, but behind the scenes, they’re not always good at paying their taxes on time. And sometimes their bookkeeping and accounting is disorganized and chaotic. And so I had a lot of people coming to me, their licensed real estate agents saying, who do know is a good CPA? Who do you know is a good accountant? Who do know is a good bookkeeper across North America? And a good friend of mine, Carl Gould, who’s now my general partner

in smashing numbers with my partners, he said, what do want to do about it? I well, nothing. That’s not my lane. He goes, what if it could be? What if we could go out and start acquiring bookkeeping, accounting, tax-paying, payroll services companies across North America and do a roll-up? And thought, great. So we’ve completed multiple acquisitions targets across the last few years and are growing and scaling smashing numbers rapidly across North America.

Michelle Kesil (06:18)
Yeah, amazing. And is smashing numbers particularly for real estate people?

Sir Darren Jacklin (06:26)
We deal with people from all walks of life that are once you know

you’re of legal age in the United States or in Canada. We work with people right from legal age, right up to retirement from all different industries, all different backgrounds. We have a lot of business people, a lot of self-employed, a lot of business owners, lot of entrepreneurs, franchisees that work with us because smashing numbers, the owners are entrepreneurs and business owners and our staff run our daily operations or employees. So we get both worlds plus Carl Gould, myself, Tatiana Merciatus, the three general partners.

decades of history and experience and results of growing and scaling companies and doing very, very well. So not only does Carl and Tatiana have the academic background, I have the street smarts. We have a lot of practical knowledge. And so we can advise people at a very high level where they pay a lot of money to consultants within smashing numbers ecosystem. We can help grow and scale companies very, very efficiently and effectively through our ancillary services offerings, but also through our team approach of what we approach people because we’re relational versus transactional.

A lot of the industry is transactional because it’s based on numbers, right? But we believe in building relationships where we help grow and scale these companies that are our clients with smashing numbers.

Michelle Kesil (07:34)
Yeah, and what do you feel have been some of the main keys that allow your business to grow and run successfully?

Sir Darren Jacklin (07:40)
Great question. Integrity, number one, being our word, accountability, responsibility, authenticity and transparency. That’s a big thing for us. And also when we have clients with smashing numbers, we create raving fans. We want to give them the Ritz-Carlton experience. We know there’s lots of other competitors out there doing taxes, doing bookkeeping, doing payroll. We know that, but we want to build a personal, intimate, trusted, connected relationship with our clients of smashing numbers.

So they get to know us, us and trust us because we’re intimate with their financial, sensitive, confidential information. And we know that they take that very seriously. So with Smashing Numbers, we want to make sure that we are in the driver’s seat with them to help them because they have to make tough decisions as they grow through their life, you know, marriages, divorces, deaths, business partners, making investment decisions and things like that. So we want to journey with them through their life with Smashing Numbers to make sure they’re making the right decisions, they’re mitigating risks.

They’re taking advantage of tax strategies and tax options, but also make sure things are organized so that they’re growing a business. Now, is it important to grow a business? But if they ever want to sell that business and expand that business, we want to make sure that that’s prepared properly for the discovery and due diligence process later on in their life. And so we want to make sure step by step everything is done correctly and done right at the highest levels of best in class business practices.

Michelle Kesil (08:57)
Yeah, absolutely. And how are you focusing on your real estate business? there any goals or opportunities that you have there?

Sir Darren Jacklin (09:08)
Yeah, great question. So I love solving problems. Everybody needs a place to sleep. And so I love finding opportunities where I can help people. So like we do rent to owns, lease to owns with some people across the United States, know, immigrant families that are coming to the United States that don’t have citizenship yet. You know, I’m Canadian by birth and I live primarily here in Vancouver, Canada is my, I travel the world all the time, a few months, a year, but I like helping people and solving problems. And I believe that the American dream is still alive. believe the Canadian dream is still alive.

So I love giving people a chance because, know, me, for example, just practically speaking, I’ve had some challenges where my back’s been against the wall. I’ve had some financial pressures, some challenges in my life where strangers believed in me when I sometimes didn’t believe in myself because I lacked the self-confidence because I was failing. I wasn’t winning. And so I believe it’s always important to give people a second chance and back them and believe in them when they don’t believe in themselves. And sometimes it’s pretty scary when somebody comes from another country and immigrants to a country, they don’t speak the language.

They don’t know the laws, they don’t know the rules, they don’t have a network or a community of like-minded people. They have to build that up over time. So it’s always important to never forget where we come from, but always help people and push up people. So I’m big on pushing up people. And that’s why I love buying real estate, because it’s a physical bricks and mortar asset. But guess what? It’s a great asset to make a difference in people’s lives and to grow financial wealth for me to then go to philanthropy to build schools around the world.

Michelle Kesil (11:01)
Yeah, absolutely. And what have been some obstacles or challenges that you’ve overcome and learned from in your career?

Sir Darren Jacklin (11:11)
Great question. So hiring people is a big challenge because sometimes, you know, I need to fill a position. So I hire someone right away versus taking the time to get to know that person, doing the due diligence, verifying, doing reference checks and then finding out that, you know, a few months down the road or several months down the road, that wasn’t the right person for those roles, responsibilities and accountabilities. So hiring right. So you hire slow, fire fast was a good thing I learned. other thing is, is if we’re raising financial capital, make sure that we have the right financial capital partners on board.

And so it’s taking the time to go through my own discovery and due diligence process, checking people out and knowing that it’s the right financial investment opportunity for what we’re doing. And also knowing the investors timeline, because there’s three types of money in life. There’s calm money, cautious money and nervous money. And I always want to know if somebody is going to invest with us that their money is a calm money. And so over communication, ⁓ having regular updates, being transparent, being authentic, being vulnerable and being an integrity being our word is so important.

And so that’s why I’ve learned. And then also too is creating an environment where people want to win, right? Because there’s a lot of negativity out there. There’s a lot of challenges on social media that we see. So you want to create a positive, supportive environment where people feel self-empowered, that they’re winning and they’re doing something positive to serve the greater good, to make a difference in humanity.

Michelle Kesil (12:29)
Yeah, absolutely. And what are you most focused on solving or scaling to next?

Sir Darren Jacklin (12:36)
Yeah, great question. So smashing numbers right now is my primary vehicle right now I’m focused on is acquiring bookkeeping, accounting, tax plan and payroll services companies across the United States of America and Canada and growing and scale that to a multi eight figure company. And we may look at an exit down the road, but right now growing it to me to get to 50 million annual recurring revenue is my personal target. I like that. And I like to solve problems and serve people and make a difference. I love working with business owners and entrepreneurs.

and having them come into smashing numbers and helping them solve for their problems. Because in life as human beings, we’re either coming from a problem, we’re in a problem, or we’re heading towards a problem. And I always share transparently with our clients that look at, problems are never gonna go away. We’re always dealing with problems personally or professionally. That’s the condition of being a human being. The thing is that you don’t, people say, well, I don’t wanna wish for more problems. No, what you wanna wish for is more skills. Because when you have more skills around the right people to advise you as a mentor, as a coach, and have a seat at your table.

Then when a problem comes up, you’re bigger than the problem. And so you want to get around people who can teach you at a higher level on how to solve those problems so they become speed bumps, not big boulders in your life. So I love doing that. I love solving problems and serving people, making a difference, and helping them get results.

Michelle Kesil (13:50)
Yeah, amazing. And are you focusing on growing and expanding and investing as well?

Sir Darren Jacklin (13:57)
All the time. I’m always looking. I’m a cashflow investor, so I don’t like speculation. I like to know when I can count things at the end of the month. So my focus is to earn money or make money, collect money, protect it, and then multiply it just repeat the process all over again. So I’m a cashflow investor, so I don’t do cryptocurrency. I don’t do anything that’s speculative. I like to know at the end of the month, I’ve got cashflow coming in from that business or that real estate assets, and then I can count it every month. That’s the key thing is that, you know, ⁓ you can’t eat your net worth. You can only eat your cashflow.

And I’ve been a multimillionaire on paper years ago, but I didn’t have any money in the bank. So on paper, I look good with my image and ego, right? I’m a multimillionaire, but I’m broke financially. Now I focus on cashflow versus net worth.

Michelle Kesil (14:40)
Yeah, and can you explain what that looks like, like strategy-wise or process-wise?

Sir Darren Jacklin (14:45)
Yeah, so the key thing is is the key thing is proximity is power. It’s not what you know, it’s who you know, it’s who you have access to. So I always say if I lost everything tomorrow, the first step what I would do is I would get around wealthy people. I get around rich people, whether it’s going to a Fairmont Hotel, a Four Seasons Hotel or a Rich Carlton Hotel. It’s been an athlete or wealthy neighborhood. It’s been around a hiking group, a pickleball group, a tennis group, horse racing group. You know, these are you got to think about in your area where you live, where does money hang out?

And the reason why you want to look at, geographically, wherever you live, whether it’s on social media, it’s on the internet, or it’s in your town or your city or country or village where you live, where does money hang out?

Because the fastest path to cash is solving rich people’s problems. Because they will pay you for speed and execution. So what you want to do is if you want to make money quickly, you need access to capital, hang around rich people. Why? Because rich people are always looking to deploy capital, but they’re always looking to get things done and produce measurable results.

So what I always share with people is get into environments where money’s already been made, because these people want to protect money, they also want to multiply money and keep repeating the process over and over again. because here’s the thing, we don’t have money problems in life. We have thinking problems in life. There’s no lack of money on the planet. It’s a thinking problem, not a money problem. And so if you hang out with people who’ve got a lot of money, they got multiple revenue streams of income coming in through various different sources every month, and they’re looking to take that money and deploy it and get it working for them, because they don’t want to have money sitting liquid in accounts.

So get around people who doing much better than you financially and watch when you can help them solve a problem how they’ll pay you to solve that problem because they want speed and execution, they want to get things done because they want to produce results.

Michelle Kesil (17:03)
Yeah, that’s great advice. Is there any other advice you would give to someone that’s looking to get into investing?

Sir Darren Jacklin (17:12)
Absolutely. Tell the truth no matter what. Be transparent with people. Be authentic. Tell the truth no matter what. That’s the key thing I’ve learned in my life is that time will either promote you or time will expose you. It’s just a matter of time. And if you embellish things, you exaggerate about things, ⁓ when somebody who’s more educated than you that’s a high net worth or ultra high net worth investor, not only they have themselves, but they have people around them that are very smart, very educated people. It’s not their first rodeo.

And the key thing is you’re gonna get exposed if you embellish or you exaggerate things. So be transparent, put your cards on the table. People say, well, I don’t wanna do that. No, you wanna look good, but you also don’t wanna look bad, but it’s gonna cost you down the road. Just look at your bank account. So when you’re transparent with a high net worth or ultra high net worth investor, and everybody you’re looking at investing with, you just be transparent with people. And by that authenticity, people can relate to you. Because listen, I’ve been up and down lots of times in my life.

Right, so I’ve been on that roller coaster ride of entrepreneurship of peaks and valleys. So I know what it’s like to struggle and have adversities and challenges and setbacks and I can smell it I can see it other people. So when somebody’s trying to impress me, I’m thinking, wait a second here, this doesn’t seem right, right? Again, money’s calm, cautious or nervous. So my BS meter goes from being calm with this person, green light, calm, to now cautious or nervous. So now I’m skeptical, thinking, okay, what’s going on? This person’s not being straight with me. They’re exaggerating things, they’re embellishing things, I tell them the truth.

What’s really going on? Now gotta dig through my due diligence to get to the source of what’s really going on. And I don’t wanna play this game of back and forth. I just want somebody to be straight up with me. Be uncomfortable, face the fear, take your mask off, your cards on table and just say, look, you know what? Right now I’m struggling, but man, I am fricking excited. I am determined. I’m going to succeed no matter what. I don’t care what obstacles, what challenges I got right now. I got no money in my bank account, but I am gonna persevere no matter what. The only way this is gonna stop me is if I die.

I’m going to take that hill. I’m going to go for it. And an investor will see your drive, your commitment, your accountability, your responsibility, your determination, and your perseverance. And that’s what their investment is. Can this person deal with obstacles? Can they deal with challenges? Can they deal with setbacks? Because everybody can sell the dream. But how do you handle challenges when things aren’t going well? That’s what an investor wants to see is how are you going to handle the bad times, the challenges. Because they’re going to come. We all go through seasons of life. And we all go through winter.

And that winter is different period of time for every person. And so right now that person might be selling summer. ⁓ it’s sunny out. It’s nice. Man, I’m doing great with my startup or my business. Or man, I got this deal for you. But what happens in wintertime? And that’s what we focus on is how does the person handle the pressures of winter?

Michelle Kesil (19:52)
Yeah, definitely that’s important.

And so what are you most excited about right now in your business?

Sir Darren Jacklin (20:03)
You know, I’m most excited. I love doing acquisitions. I love the opportunity of solving problems and helping these men and women transition towards retirement and knowing that with smashing numbers that we’re going to take great care of their clients, take care of their employees, take great care of their tenants if we buy the real estate holdings. So I’m very grateful for that. And I’m grateful to financial grow and build wealth because all my wealth goes to my foundation, Link Foundation for Global Philanthropy, which is building schools around the world. Through Link Foundation, we build schools. So I believe in profit for people.

So how do we solve problems with smashing numbers, with growing and scaling businesses by doing acquisitions and solving our clients’ problems? But I’m building this to actually have the bigger thing, which is a legacy, which is global philanthropy, which is helping to alleviate poverty, provide access to clean drinking water, food security, while enriching children’s and communities’ families’ lives around the world that are in places that they don’t have opportunities like we do in the first world. So that enriches my life and gives me so much joy and fulfillment is knowing that I can be a contribution.

and make a difference and take people along with me to be of service and make a difference in humanity. Because my success or our team’s success is someone else’s miracle.

Michelle Kesil (21:12)
Absolutely

amazing. Thank you so much for sharing all of that

Sir Darren Jacklin (21:14)
Mm-hmm.

Michelle Kesil (21:17)
Before we begin wrapping up here, if someone wants to reach out, connect, and learn more, where can people find you?

Sir Darren Jacklin (21:24)
Yeah, do you want to learn more about smashing numbers? You can go to SmashingNumbers.com SmashingNumbers.com and if you want to reach out to me directly you can go to DarrenJacklin.com and all my information is on there or you can look me up on social media under Darren Jacklin or Sir Darren Jacklin

Michelle Kesil (21:39)
Perfect, well appreciate your time and your story. Thank you so much for being here.

Sir Darren Jacklin (21:44)
I’m grateful to be of service.

Michelle Kesil (21:46)
And for the listeners tuning in, if you got value, make sure you have subscribed. We have more conversations with operators who are building real businesses and we’ll see you all on our next episode.