How a Lawyer-Chef-M&A Specialist juggles three full-time careers
Meet Simar Anand, who turned personal tragedy into purpose by preserving legacies across law, restaurants, and acquisitions
Hey, it's Alex!
This week, I'm chatting with Simar Anand — a lawyer by day, restaurant owner by night, and search fund operator in between. After losing his father to COVID-19, Simar took over the family restaurant rather than closing it down, despite already having a successful legal career.
Rather than pursuing work-life balance, Simar embraces a philosophy of harmony and acceptance across his multiple ventures. From hiding his restaurant work from his law firm to now openly building multiple businesses that preserve legacies, his story demonstrates how purpose and intention can transform impossible workloads into meaningful pursuits.
If you've wondered how to pursue multiple passions without burning out, this conversation is packed with wisdom.
Dive in below!
Quick Stats:
🤝 Businesses: Corporate law practice, restaurant, acquisitions search fund
⚖️ Law Practice Team Size: Solo practice (previously at a large firm)
🍽️ Restaurant Established: 2001 (Taken over in 2020)
👥 Restaurant Weekly Covers: ~200 customers per week (40 per night)
💰 Restaurant Annual Revenue: $500-600K
📊 Restaurant Profit Margin: 8-10%
🔎 Search Fund Activity: Reviewing ~22 CIMs monthly
📍 Location: Montreal, Quebec
Managing multiple careers…
First off, let me preface by saying, I'm not trying to chase work-life balance here. I'm curating my energy in a way that allows me to focus on what's most important in that moment.
And that's how I get through my day.
Juggling three very unforgiving careers, right?
Being a lawyer alone is a full-time job…
Being a restauranteur alone is a full-time job.
Trying to find a business to acquire and setting up a search fund is a full-time job.
I've given up on chasing work-life balance.
Balance means symmetry…There's an equal amount of both.
And it doesn't have to be that way.
There are some days when I'm more lawyer than I am chef.
There are some days when I'm more chef than I am lawyer.
There are some days when I'm more son or boyfriend or grandson than I am any of the other two things.
You really got to be present in the moment.
And before we get to the how, I think I have to ask myself why, right?
Because if the why is strong enough, right, the how will figure itself out on its own.
For me, law fuels my mind.
The mental gymnastics and arithmetics that I have to do to develop a strong position for my clients when we're negotiating something with the opposite side – that exercise fuels my mind.
And then at 4pm I pack up my laptop, throw on my chef's coat, and make my way to the restaurant.
And I rest.
I spend the rest of the evening feeding my soul.
To that balance between fuelling my mind and feeding my soul is my why.
I think life is too short to spend your entire life just doing one thing over and over again on rinse and repeat.
Being on my feet at all times and spending most of my day putting out different fires – I live off that energy.
And I need both to feel complete. For me, doing just one would be incomplete.
The journey from corporate law to entrepreneurship...
Pretty simple kid. Born Montreal, lived in Montreal my whole life.
Quebec was not as open and embracing of other cultures then as it is today.
I grew up in an anglophone part of town, a lot of my friends were all francophone, and at home I was speaking Punjabi. So there were always at any given moment three or four different languages going on in my head.
I got picked up and brought to my dad's restaurant after school.
I grew up most of my life in my old man's restaurant, helping him with the business.
I always think back to my time being involved in the family restaurant and it gave me early lessons in obviously hospitality, but also resilience and building connections with people.
That's the one thing that I think has really held my hand and gotten me through so much in life outside of the family business.
I ended up at McGill, studied finance, and worked in finance for a bit. W
orked for the Department of Commerce for the United States government advising on foreign trade and bilateral relations.
Little fun fact – the department of commerce, at least out of the Montreal consulate, shares an office with Homeland Security and so most of my day was spent in a bomb shelter underneath the embassy. It was a really cool experience seeing how government works and diplomacy works from that angle.
Eventually law school happened at the University of Windsor. I packed up my life in a suitcase and moved to Windsor. That was a bit of a culture shock – being a big city boy, then moving to Windsor.
I had spent most of my time in law school thinking I was going to be a human rights lawyer. I was going to fight for the underdog and fight for people's rights and stick it to the man.
Then during recruitment season in second year of law school, I had one of the biggest corporate law firms in the country dangle a really shiny carrot in front of me and say, "Hey, come work for us" and be a corporate lawyer. I accepted, and the last seven years after graduating law school, I spent most of my time working in a corporate setting as a corporate lawyer.
I describe myself as your friendly neighborhood corporate lawyer today, but it really is fulfilling.
We have such interesting people walking through my doors every day who have brilliant ideas and are trying to find ways to start businesses around those ideas, commercialize them and bring them to market.
A lot of times the ideas they're coming to me with are very impactful ideas that can do good for the world.
If I could be a small part of that equation, advising them from a legal perspective on how to grow and scale their business so that it can have greater impact in the world, I think I'm still doing meaningful work.
Preserving family legacy through the restaurant...
Unfortunately in the first wave of the pandemic I lost my father to COVID. Young guy – he was 55 years old when he passed away. COVID got to him early before it even had a name and there were any vaccines out there.
This beautiful restaurant that I had grown up in, that he had built from the ground up when he left India and moved to Canada – this beautiful restaurant sort of fell into my lap overnight.
Every person and their mother was telling me "close down the restaurant. You don't need it anymore. You've got a very successful career. You're a big shot corporate lawyer on Bay Street."
They said the restaurant is a fixture of the past and it's not something that you need today.
But there was something inside me that said, "I am who I am today because of the lessons that I learned in that restaurant. I am who I am today because of the work ethic that I saw in my father as he slaved away in the kitchen every day chopping onions."
And so I had to figure out a way to keep that going.
I found so much fulfillment in preserving my dad's legacy in the restaurant.
The exercise of preserving and growing legacy can be very fulfilling and I wanted to find a way to multiply that.
When I'm at the restaurant, when I'm running a dinner service from 5:00 to 9:00, I'm not just sitting back there cooking food.
I'm trying to preserve a legacy and grow a legacy for that matter.
Extending the legacy concept through a search fund...
That legacy preservation piece is also what motivates me in my search fund and getting out there and finding businesses to acquire.
They're all connected somehow.
In the way I'm preserving legacy in my dad's restaurant, I also want to find other family businesses, small to medium-sized businesses that operate on very robust business models and have a lot of potential but don't have the right succession plan in place.
I want to support those businesses in preserving and growing their legacies by taking equity stakes in their companies.
We've got very clear criteria that we're measuring and assessing every business against. There are hard financial criteria – it has to have a certain EBITDA, a certain growth margin, it has to have a certain number of employees, it has to have been around for a certain number of years.
But then there are some of the softer criteria as well.
What is the potential for this business to have a more positive impact on some of those external stakeholders?
I've been searching for that first acquisition that our search fund is going to make for eight months now and I still haven't signed a single LOI (Letter of Intent).
I had lunch with one of my mentors in this space a couple weeks ago and I was telling him, "George, I am reviewing CIMs day and night. I'm reviewing term sheets day and night outside of advising my clients on legal matters and cooking up a storm at the restaurant."
That's what I spend the rest of my time doing – reviewing these business opportunities, but I can't find the right business to acquire.
His response to me was, "Well, then you're looking at it the wrong way. Why are you looking for the perfect deal? You're never going to find the perfect deal. The perfect deal doesn't exist."
"In fact, if the deal is so perfect, my advice to you would be not to buy it, not to pull the trigger and sign an LOI or submit an LOI because there's no value that you can add if the business is so perfect. You want the messy businesses. You want the ones where there are gaps in efficiency. There are things that need to be addressed."
So that's another criteria that we've now added to our list – what are the businesses that are typically run inefficiently, haven't caught up to the advancements of technology, or haven't found leaner ways to operate.
We're going through an environment in the next 10 years where a lot of these SMBs (small to medium-sized businesses) will shut down because they have no succession plans in place, and that's an opportunity.
Empowering these SMBs to continue in some way or another, whether it be with a different management team in place but keeping the owner-operator on as a passive shareholder, finding ways to continue those legacies – it's one thing I'm already working on day and night at the restaurant.
And the type of law that I practice is M&A, so oftentimes my clients are either buying or selling their businesses.
It's already something I'm empowering my legal clients to do in the way that I give them legal advice, whether that be on a buy-side mandate or a sell-side mandate.
So it all ties together, even if it seems random.
Building effective teams and mastering delegation...
I am able to do what I'm doing today because I've got great teams.
Like I said, I could sit here and talk about time management, but there's so much more to it.
Building the right team to support you – there's so much that goes into making sure you're picking the right people that you're surrounding yourself with and they're all rolling in the same direction.
I have this philosophy that one of my senior mentors once described to me, and I've adopted it for God knows how many years now – I am constantly trying to find ways to be the dumbest person in the room.
And that includes my own team members, whether that be at the restaurant, in my law practice, or the interns that I'm bringing on to help with my search fund. You always want to be the dumbest person in the room, and not try to suggest that you know it all.
When you're building these teams, it's making sure that everyone that's on this boat with you understands that you are rowing in an environment that allows for mistakes.
Making sure everyone appreciates that no one is expecting perfection — that's how you find the right people. Now, if you've got people on your team who understand that it's okay to make mistakes, but once a mistake is made, look at that as an opportunity to learn and grow from.
Mistakes are OK, but if no one's looking at that mistake as an opportunity to learn, and then that mistake is being repeated, there's a different conversation that needs to be had.
I come from an environment, especially in corporate law, where that wasn't necessarily the case. It's a high pressure environment where a mistake can result in millions and millions of dollars of lawsuits.
That's a reality – I don't actually exaggerate that.
When we're drafting these contracts where there's a lot of money on the line, not building in the right language in a provision can cost a lot of money, so perfection was expected.
But I try to make sure people are comfortable, and delegate enough responsibility to an individual where they feel like they have skin in the game.
It's really hard to find employees who will operate a business as if it's their own.
They may not be like that day one, but I try to instill those values into those employees – "Hey, I'm expecting you to run this business as if it were your own business. You're not just an employee here."
That "carrot" will look different for different types of people. For someone like me, when someone gives you a certain responsibility, you will go the whole nine yards to make sure you fulfill that responsibility to the best of your abilities.
That alone is enough of a carrot – that I’ve been entrusted with a responsibility.
For others, there are financial metrics and incentives that you can put in place. I'm currently in the process of negotiating a profit-sharing agreement with one of my managers at the restaurant just to align our interests a lot more.
We're building out a new arm of the restaurant business – catering.
I've asked one of my managers internally to lead that effort, and we're going through the process of negotiating how she will be compensated.
Using time with intention...
I heard someone once say that if you're really good at time management, you can pick up a lot more hours in the day. Time will begin to stretch when you're good at time management.
I don't know if that's necessarily true — everyone gets the same 24 hours…
But I do think time starts to become more elastic when you use it with intention.
If you are looking at the hour ahead and you're saying, "I'm going to spend this next hour present with the intention of achieving X or Y…"
I think you end up achieving more in that same hour than you would otherwise.
It's not like you're getting more hours, but if you can shut off the distractions, you can make the most of the little time you have to apply to that problem.
So, if I've only got an hour in the day to look at a term sheet, I'm going to give it my all.
I might have to put it aside after 45 minutes and pick it up again later, but those 45 minutes will be dedicated to just that.
I am a bigger proponent of acceptance and letting go of this concept of perfectionism.
Trust me when I tell you this, I have missed enough deadlines in my life…
I've made enough mistakes.
But I start every day with a clean slate and I tell myself that the next 24 hours are an opportunity for me to learn and grow regardless of how they go.
Embracing imperfection as part of the process is huge for me.
Building relationships for business development...
There are a couple of different ways I build the pipeline for my search fund.
I've got access into a network of entrepreneurs, owners, operators who I advise from a legal perspective. That allows me to gauge when I think they'll be ready to sell and whether I will be the buyer on the other side of that transaction.
The second way is building really good relationships with accountants. So much of my day is spent reaching out to accountants.
When a person is ready to sell their business, the first person they talk to is their accountant.
Making sure I've built good enough relationships with these accountants so that they could send their clients my way when they need legal advice, but also when they're ready to sell, so that I get first dibs on reviewing and analyzing the opportunity.
The third way is probably the hardest, but the most enjoyable, is picking up the phone and calling owner-operators and just shooting the shit with them.
These owner-operators are so caught up in the day-to-day operations of their business, they rarely get an opportunity to take a step back and talk about the future of their business and talk at a higher, more strategic level.
Eventually the goal is to build a strong enough relationship with these owner-operators that when they are prepared to sell, they're thinking of me.
And sometimes the conversation ends up going in the direction where they never even thought of selling, but you're convincing them that now is the best time more than ever to sell.
Part of my exercise in the last couple of months has been connecting with the chambers of commerce within a number of areas and saying,
"Hey, you have a membership of 200 to 500 businesses in your area...I'm a lawyer.
How would you like if I gave a 45-minute webinar or presentation to all of your members for free?"
Nine times out of 10, they're like, "Absolutely. Come on in. If you want to talk to our membership about how to navigate the current tariff environment, please do so."
All of a sudden I now have an audience of 200 businesses.
There must be someone in that pack that's thinking about selling…
And so it's getting in front of these businesses, building relationships with them, encouraging them, inviting them to reach out to you down the road if they're thinking about selling or if they have any other legal issues.
In that way, I start to build a pipeline of businesses for the search fund as well.
When we walk into rooms to pitch people on what we can offer them, we try to outsmart them or make it sound so complicated to instill fear in them.
That turns people away more than anything.
So much of what we do in our lives, whether we are chefs, lawyers, or people working in finance or entrepreneurs – so much of what we do is storytelling.
People often over-complicate the story.
Make it as simple and crystal clear and straightforward as possible and you will generate far more leads than anyone else.
Meaningful impact through business ventures...
We often think improving society is the role of government or non-profits.
And we've created a world for ourselves in which profit is antithetical to well-being and leaving the world a better place than the way we found it.
I've been a big proponent – and people are starting to turn their minds to this – that when it comes to leaving the world a better place, it's actually not the government that's going to make any difference.
It's the private sector…
It's the businesses that, if operated in the right way – less exploitive, less extractive and more regenerative – can really change the trajectory of our communities.
Especially in the current economic environment, its becoming obvious small to medium-sized businesses are the engine that drive our economy.
I think that's what I want to spend the rest of my life working on, whether it be through the restaurant, my law firm or the businesses that I acquire through this fund.
I want to see how each of them can work within their communities in a way that leaves those communities better than when they first started.
One book recommendation I'd make is 4,000 Weeks.
I've read it twice.
It describes productivity and time management within a certain context, and that context is, dude, you've only got 4,000 weeks to live.
It really forces you to take a step back and reprioritize and reallocate your energies in ways that make sense and align with your goals and values.
It's actually forced me to slow down a little rather than speed things up because the clock is ticking.
I encourage everyone to take a crack at it.
THIS! Completely resonates. Thank you!!!!