Accounted For

Join in for a conversation with Justin Jackson, Co-Founder of Transistor.fm. It’s a podcast hosting service and full disclosure, Accounted For is hosted on Transistor. I learned about the company and Justin because Basecamp’s podcast is hosted on Transistor and I further learned how Justin bootstrapped Transistor 2 years ago to a company that generated monthly recurring revenue exceeding $50,000. Justin didn’t start out in tech or podcasts but working for a not-for-profit for the first 7 years of his career. In our chat we dive into Justin’s decision into switch into tech at 28, navigating a career to product management in tech startups, starting his first company, building a community with podcasts and his journey with building a successfully bootstrapped SaaS company.

Join in for a conversation with Matt Cohen, Founder & Managing Partner of Ripple Ventures. Ripple Ventures is a Toronto-based early-stage venture fund that works alongside startups through the good and the bad every day. Fitting with their motto of “Operators First” per Matt’s background as an operator turned investor. Though before Matt became an operator, his career started in finance as an equity trader for RBC, completing tours on Wall Street and Bay Street. While working in capital markets, he made a seed investment in Turnstyle Solutions, cutting his operator’s teeth on the company’s journey to getting acquired by Yelp. We go through the various pivots in Matt’s journey from capital markets, tech operations, angel investing and to his current role of running a venture capital fund. As always, it was never a pre-planned linear journey and we dig through every part of it.

Join in for a conversation with Terrance Kwok, Product Manager at HyperComply. Terrance was one of the pivotal folks who recruited me to KPMG to start my accounting career. It’s been a while since then and today we go through Terrance’s journey from leaving accounting just before getting the Chartered Accountant designation to join a young Vidyard, before it became the 150+ tech company it is now, in an entry role in sales. We explore how he pivoted from sales to product management, working remotely in London, UK while working for a company based out of Kitchener and his subsequent journey being a digital nomad product manager at Chilipiper and HyperComply. This was a super fun conversation where we dove into what it was actually like to make each pivotal jump in Terrance’s career and how shame, embarrassment and doubt are all real and even normal emotions when you go through an unconventional career. Please forgive me on places where the audio quality isn’t as great as with COVID-19, Terrance was taking refuge in a hotel where the connection wasn’t the best. But, I promise it won’t change how fun this conversation will be for you!

Join in for a conversation is another anonymous podcast with a return guest from episode 29 where we turnover the rock of working in a hedge fund in Canada. This was a top 10 downloaded episode in 2019 so what better way then to bring on my guest back during a time of market turmoil to see how it’s been like being an investor at a fund. Turns out, my guest already has an anonymous profile in the finance Twitter community as Moatsixcap. We chat about what it’s like being a fund manager during a time when the stock market plummets 30%+, deeper into what my guest is investing in, interesting companies worth digging into, and much more.

Join in for a conversation with Josh Broun, Co-owner of Impact Kitchen. Impact Kitchen is a wellness company with 4 restaurants in Toronto. I’ve been a fan of Impact Kitchen since it’s first location at King East and I’ve been a patron here at least once a week for the last few years. It’s one of my staple places for legit healthy meals. My go-to is the paleo waffle though. A comfort food. So it was a real treat to speak with Josh, the man who helped create a place where I could get awesome coffee, work out of for a few hours, have some high-quality healthy food, in an awesome atmosphere. Josh’s journey did not start as a restauranteur. A hint, it involves going to university on a baseball scholarship in the US, studying health science, pursuing teaching, then firefighting, then becoming a personal trainer for successful entrepreneurs. Josh rekindled an inner entrepreneurial fire while getting a masterclass on business from his clients as he learned about their lives over the years. Through our chat, we go through the stress he felt early when he didn’t feel like he had his life figured out at 25 to the journey of starting Impact Kitchen at 35 to what it’s been like in the last 5 years of building the business.

Join in for a conversation with Elvis Wong, Founder and Managing Director of Innovate Financial Health (IFH). IFH is a not for profit accelerator based in Toronto that works with start-ups addressing the problem of financial health for financially vulnerable Canadians. Having developed a passion for social impact since high school, Elvis leveraged his experience as a management consultant to join the MaRS Studio Y Fellowship program to find ways of using technology to create social impact. What he did not expect was that he would be solving a problem in wealth inequality that would lead him to opportunities working with Social Capital Partners, one of the leaders of impact investing in Canada, and starting an accelerator backed by JP Morgan Chase and Capital One. In addition to dissecting his journey to creating IFH, we dig into the various learnings he has had from building an accelerator and strategies for forming partnerships with large corporations.

Join in for a conversation with Miguel Fernando, the Founder of Moment Financial. Miguel navigated a career starting in international finance to building products in FinTech companies to becoming a full-time bootstrapped entrepreneur. Miguel started his career in finance as an economic researcher at RBC and moved over to international wealth management with a focus on Central and Latin America. He made the pivot to work in a product role and become a product manager after realizing he enjoyed building internal tools and solutions while working for the bank and made the leap to join a FinTech company while teaching himself product management and coding through bootcamps and online courses. He went onto build the advisory solutions product for Purpose Investment’s Purpose Advisory Solutions business and made another leap into entrepreneurship. Something he felt he had to do. We talk a lot about the early years of entrepreneurship, what it was like making the decision, what gap he saw in the market, and much more.

Join in for a conversation with a return guest, Marc Champagne. Marc is the Co-Founder of Kyo and Host of Behind The Human Podcast. In episode 46 we talked about Marc’s journey of building Kyo after a career in pharmaceuticals. In today’s episode, we talk through the developments since the year. The process and reason behind shutting down Kyo, the digital journaling app that had 86 million impressions and a community of 200,000 users. We talk about the difference between app rankings and user metrics vs. the economic reality of operating it. We also talk about Marc’s journey of building communities and how the podcast led to so much more than a personal brand, his new pursuit of consulting human-centric companies on brand strategy and writing a book on mental fitness. Traditional media only touts the stories of exits for obscene financial numbers but in our conversation today we talk about the daily process of building something, the constant ups and downs and the many iterations we will make in our journey to build something that is meaningful and fulfilling.

Join in for a conversation with Alex Norman, Co-Founder of TechToronto, Head of Canada for AngelList and Partner of N49P Ventures. Through his various ventures and roles, Alex is an investor and tech entrepreneur who is building the Canadian tech ecosystem. TechToronto is on a mission to develop the technology and innovation economy in Canada through its wide-reaching events. AngelList is the startup investing platform that manages $1.8Bn and N49P is a VC fund for early-stage companies in Canada. Prior to these ventures, Alex was an investment banker for Lehman Brothers during the dot-com bubble. He worked in various startups in SF, NY and London, UK. He received his MBA from Wharton, became a management consultant for McKinsey and co-founded Homesav, one of Canada’s largest furniture e-commerce companies, that was later acquired by Rebellion Media. Given how interesting his journey has been, we talk through how he made decisions in each of his career pivots and the circumstances that existed at the time. We also cover what the early years of building communities are like, the mistakes he’s learned from, and his own unconventional beliefs.

Join in for a conversation with Ben Yoskovitz, CPO and Founding Partner of Highline Beta. Highline Beta is a venture capital and startup co-creation company based in Toronto. In our interview, we pan through Ben’s 20 year career as an entrepreneur, angel investor and startup executive. After graduating with a psychology degree, Ben started by building a web service business then a product based business and one of Canada’s earliest accelerators (where one of its companies was acquired by Airbnb). He then went to become the VP of Product at GoInstant and VarageSale while co-authoring The Lean Analytics book that’s been translated to more than 4 different languages. We go through the major learnings his had from his various ventures, his failures, his philosophy of building organizations and so much more!

Join in for a conversation with Daniel Francavilla, Founder and Creative Director of Now Creative Group. Now Creative Group is a creative agency based in Toronto the builds brands and tells stories through impactful design, digital, marketing and media. In our chat, we go through Daniel’s journey from a freelance graphic designer in high school to starting his own agency after graduating from OCAD. We talk about Access, his first entrepreneurial project he started in high school and is in its 13 year of operation to specific pricing and client-related tactics in running a creative agency and his process of focusing on strengths in business and life. Daniel received the 40 under 40 award in 2018 and I could understand why from what he has build in his creative and social impact ventures.

Join in for a conversation with Jaxson Khan. Jaxson is the CEO of Khan & Associates, a consulting firm that focuses on AI and FinTech. As a result, he also is a co-host of an AI podcast called Ask-AI. I reached out to Jaxson after learning he had left his role as the Head of Marketing at Nudge.ai, a startup in Toronto, to live remotely in Columbia where he was getting paid to write in-depth articles for companies. Needless to say I wasn’t disappointed when we met to have the interview as I learned about Jaxson decision to not take a prestigious consulting offer but take the start up path early to why he started his own consulting firm. We also discuss what the early years of running his own service-based company has been like, the lessons he learned, what he would do if he had to do it all over, and how he builds and strengthens relationships.

Join in for a conversation with Karm Sumal, CEO and Co-Founder of Daily Hive. Daily Hive is a national news media company that started out in Vancouver as Vancity Buzz and now has offices in Calgary, Montreal and Toronto. As a site that started in 2008 amid a competitive industry with many regional and national giants it garners as much as 17M page views a month. Not too shabby for supporting a country of 30M. Karm did not dream of owning a digital media company. Born to immigrants in the East side of Vancouver, he became a CPA and controller for Blenz Coffee for the stable job. But him and his cofounders felt the Vancouver news media didn’t cater to the Vancouver he saw. The Vancouver that was made up of middle class immigrants that make the city what it is today. This started the 12 year journey of Daily Hive. In our conversation we talk about his early years of starting Daily Hive, what learnings he carried over from large corporation to running his own company, the media landscape and the constant ups and downs of operating a national media company.

Join in for a conversation with Jim Elli. Jim is a powerlifting coach and marketing manager of Reactive Training Systems (RTS). RTS is an online coaching company that leverages its founder, Mike Tucherer’s method of auto-regulated strength training and they’ve trained multiple world champion powerlifters. After reading Mike’s work and following some of their world-level powerlifters, I signed up to work with for the last 2 years as I rehabbed back from my knee surgery. Today conversation isn’t about my journey though but about my coach Jim’s. We go through Jim’s journey of setting up his own online coaching practice prior to RTS, how he dealt with imposter syndrome as a business major who became a powerlifting coach, how he moved from running his own coaching company to join his dream team at RTS and the entrepreneurial journey of being a remote, online powerlifting coach. For those of you who are non-health science folks that are passionate in sports and helping others, this may be right up your alley but even if you aren’t, it will be a story that can inspire you to find the thing you love and do whatever it takes to make it work.

A blast from the past to start the new year. Join in for a conversation with Stephen Shedletzky, Head of Brand Experience and Igniter at Simon Sinek. If that name is familiar with you it may be because you may have watched Simon Sinek's famous TedTalk or read his first book "Start with Why". Stephen joined Simon Sinek's company, called after his own name, as the 4th employee 7.5 years ago. Stephen's journey to help people feel more fulfilled and engaged by the work they do started when on his first day on his first job at Suncor's leadership program when they fired 1000 people post-merger. This propelled him on a journey to find how he could do his life's work. We chat about the fruitful departure from Suncor, his foray into human capital consulting, why his tenure there was even shorter than at Suncor, starting his own platform for change as a personal 2-year MBA, the 5 paragraph email that got him a call with Simon Sinek and how his journey with Simon started a new chapter in his life. My first meeting with Stephen was when he graciously invited me to attend a talk he was giving at an incubator and though that was a treat it was nothing compared to the intensely fun discussion I got to have with him on the podcast. It was a super fun conversation and we also spoke about maybe even doing a part two in the near future so if you liked it please let me know on my sites contact page.

A blast from the past with a replay of the most popular episode of the quarter. Join in for a conversation with Nadeem Nathoo, Co-Founder and Executive Director at TKS (The Knowledge Society). The Knowledge Society is an education company that works with 13-17 year-olds to mine human potential to make unicorn people. From cold-emailing his way into an internship with, Nobel Peace Prize winner, Muhammad Yunnus' Grameen Bank at 19, to being part of the first cohort of the Next 36, travelling throughout Africa at a young age, entrepreneurship and social impact was a major part of Nadeem's growth. After working as a consultant at McKinsey, Nadeem plunged into the world of entrepreneurship by joining up with his brother in San Francisco. It would be a hypothetical question of what they would do with $10 billion that propelled the creation of TKS back in their hometown, Calgary. Nadeem and his brother created a company that combined their love for learning and exponential technology and it's a journey I've had a lot of fun learning about.

Join in for a conversation with Alex Castellani, Co-owner of Boxcar Social and veteran coffee professional. Boxcar Social is a cafe and bar with 4 locations in Toronto and 1 in Halifax and one of my go to places for some light acidic coffee. Alex got degrees in business and philosophy but instead of embarking on the path of an academic, he would make coffee his career through some fateful encounters from living in Vancouver to taking a break from school. We talk about his journey of building and growing Boxcar Social with his three partners, the state of coffee in Canada, the coffee value chain and more! We touch upon the tactical and philosophical in the world of coffee, food and entrepreneurship.

Join in for my second anonymous conversation with the accountant turned UX designer from episode 60. Thanks to you my listeners writing in: we answer questions on whether having a bootcamp credential adds any value if your portfolio is already good, difference between college programs vs. Bootcamps vs. doing it by yourself, skills to prioritize to set yourself apart, why there are more senior design positions vs. junior ones, whether the guest would do the bootcamp again and learnings to make the process smoother.

Join in for a conversation with Hans Arijanto, Product Engineer at Angelist. We have a dual segment episode today. The first half talks about Hans’ career from working in startups in Toronto to Silicon Valley to Jakarta and back to Toronto. We dive into the various transition points in his career, why he left Facebook for a startup, how he ended up working for the Tokopedia, Amazon of Southeast Asia, and owns a board games cafe. Then, we go into a second part that is a new concept I’m trying out called Uncommon Sense. It’s a segment where I hope to have friends on and we talk about things that may be common sense to us but not others. With Hans, we go through philosophy and the cultural differences between Jakarta, Indonesia and Toronto, Canada.

Join in for an AMA episode on Podcasting. From the numerous chats I’ve had related to my podcasting experience, I decided to answer the most commonly asked questions in a full episode.

Join in for a conversation with Shawn Huang, Founder and CEO of 36paths, a career accelerator based in Toronto. Shawn immigrated to Canada as an international student from a city 2 hours outside of Shanghai China. Despite having a family tree filled with academics in all subjects of science, Shawn decided to study business to chase an internal entrepreneurial fire that had him sell soda cans as a kid and drop ship shoes as a kid. After building a career in finance as an investment banker and product manager of a FinTech startup in Toronto, he made the leap to go full-time into his career accelerator that helps international students, like himself, get jobs in various business careers. In our chat, we talk about his journey to starting 36paths, the cultural differences between Shanghai and Toronto, and what the first 6 months of solopreneurship has been like. It’s a conversation I really enjoyed having and we get quite deep and real as we share the shit sandwich we each ate in the first 6 months of our respective journey.

Join in for a conversation with Carolyn Plater, a psychotherapist and mental health clinician who is the Co-founder of Hoame (North America's largest meditation studio) and Ease (Corporate Wellness Consulting Company). Before starting Hoame and East 2 years ago, Carolyn spent 10+ years in the mental health space as a therapist, clinician and crisis worker who worked with various mental health patients in schools, foster homes, and hospitals. Though her mother's nursing career had influenced her to dream about a career of helping people in the future, it would be a pivotal decision to transfer out of her English major that sends her down the world of psychology and mental health. Her frustration with the reactionary nature of mental health care led to starting Ease with her current co-founder, Steph, and they ventured out to create a state of the art meditation studio in downtown Toronto. In our chat, we go in-depth into Carolyn's journey, her experience with meditation, how people could get started, the entrepreneurial journey of starting a meditation studio and more.

Today is a little different. A semi-anonymous podcast. I say semi because the guest wanted to keep his identity open in case people had follow-up questions for him. My guest today is Vince and we explore his journey from the world of Big 4 audit to transitioning to be a software developer by going through a bootcamp. In our conversation we go through his process of making the jump, why he decided to do a bootcamp, the assumption vs. reality of bootcamps, the surprises in the transition and what life is like after accounting.

Today is another anonymous podcast. We go deep into the life of an experienced back-end software engineer. The interview gets quite technical as I have my guest go deep into explaining what software engineers do so that a non-engineer like me can understand. We also talk about how the guest hires and interviews engineers, the industry, and how my guest has managed to create a situation of remote working with 4 hour work weeks (quite literally at times).

Join in for a conversation with George Khalife, Head of Marketing & Business Development at owl.co, Host of Let's Grab a Coffee podcast and Co-founder of BookBack app. Having grown up in the middle east from Lebanon to Bahrain, the merchant blood and a passion for building relationships was rooted in his upbringing. Seeing the world through his father's career in finance brought him to be a finance major in university and start the student investment club at University of Ottawa. However, instead of pursuing traditional investment banking careers like his peers he went into sales and marketing. Pursuing a career in the realm of business development, sales and marketing was not a conventional option discussed in university but from listening to colleagues and observing what gave him energy George moved down the unconventional path where he saw an opportunity to merge his interests in Finance, and a newly growing one in technology as he saw the big wave of Tech IPOs in Toronto. We go through his various transitions from working at the TMX Group to investment banking and a startup as well as what someone actually does in business development. I hope my conversation with George adds value to your own career journey.

Today is another anonymous podcast. In this episode, I dig into my guest's journey of leaving the world of accounting and tax to Product UX/UI Design at a Startup. For those unfamiliar with product design, I would recommend listening to episode 20 with Jason Li who now runs a product design agency called TomYum. In this conversation, we talk about my guest's experience leaving the coveted professional service world with a manager's title, the decision making process behind it and what it was like taking a jump to the unknown without any prior background in 'creative' fields. We talk deeper in the guest's honest experience with bootcamps, the design job market in Toronto and more!

Another blast from the past. Join in for a conversation with Tom Lowden, the Labs Manager of WeWork Toronto. Prior to WeWork, Tom build out a skill set in fundraising for the public sector after having explored a number of different opportunities. After that experience he was the inaugural, I daresay the 'founding' team, of Toronto's Creative Destruction Lab incubator and he went on to become an investor and operator with Boat Rocker Ventures where he brought to life the Dineen coffee shops. Tom's fascinating career is one filled with entrepreneurial spirit and I hope you find it as enjoyable and exciting as I did.

A blast from the past. Join in for a conversation with Ian Weng, an operations and logistics manager and Vancouver market lead for UberEats. Ian and I met at the University of Waterloo and we both started our career in Audit at KPMG. Since then Ian has taken a unique journey through infrastructure investing, a food startup and then to his current role at UberEats where he has noted that Uber's unique business model makes the role very different from his counterparts in other big tech firms like Google or Facebook.

Join in for a conversation with Shubha Dasgupta, President, and CEO at Capital Lending Centre (CLC). CLC is a brokerage house for mortgage brokers in Canada that grew from just 6 in 2017 to 160+ in 2019 and is one of the fastest-growing mortgage brokers in the country. Shubha and his partner, Kendall, started CLC to be a new kind of mortgage brokerage house, one they wish they had when they started. Shubha's been in the mortgage industry for more than 10 years and before this part of his career, he started a transportation logistics business with a friend right out of high school. He entered the old trucking business as a wide-eyed 18-year-old and build a business that would be transporting toys made in Toronto all the way down to Disney World in Florida. In our chat, we go talk through Shubha's entrepreneurial journey in two old industries: trucking and mortgages, the lessons he had from starting the different businesses and how two pivotal moments that involving his grandmother and his mother altered his career and his passion for philanthropy.

Join in for a conversation with Graeme Moffat, Chief Scientist and VP of Regulatory Affairs at Interaxon. Interaxon is a neurotech company based out of Toronto. They are the creators of the Muse headband where it uses technology and neuroscience to help you meditate effectively, one of the world-leading companies making this happen. Graham earned his PhD in neuroscience at Universite Aix-Marseille in France but he had his sights set on joining the private sector during his early neuroscience education at McMaster university. He was bit by the startup bug whilst building the largest neuroscience publication platform in Switzerland and that led him to become the Chief Scientist at Meta, a NeuroTech company that got acquired by the Chan-Zuckerburg Foundation, and later to become the Chief Scientist at Interaxon. In our chat we cover Graham's fascinating global journey as a neuroscientist, the academic world, the childhood that started his fascination with the human brain and much more. I should also add that I selfishly wanted to learn more about neuroscience and meditation so we also geek out about all of that in the episode as well!

Join in for a conversation with Henry Shi, Co-Founder and CTO of SnapTravel. As the name implies, SnapTravel is a travel company headquartered in Toronto that creates a seamless experience for you to book your hotel accommodating through easy instant messaging apps. Henry and SnapTravel made the news rounds when they raised their Series A round with Golden State's Steph Curry and Henry's acceptance onto the Forbes 30 under 30 list. SnapTravel is Henry's third startup company after having created two others while at the University of Waterloo's Velocity student incubator and Canada's Next 36 program. After his first two startups, Henry decided to take a startup sabbatical by getting a low-stress job at Google. In our conversation we go through the learning Henry had from his first two startups, the decision behind working at Google, the early years of starting SnapTravel and the major mental model he uses for many of his decision makings.

Join in for a conversation with Eric Arnold, Co-Founder and CEO of Planswell. Planswell is a fintech company based in Toronto that is a one-stop shop for financial information and advice to Canadians. On his journey of starting Planswell Eric had nine other businesses. His entrepreneurial push started early with a desire to make $100,000 as a young teenager and a school environment where he constantly felt misunderstood propelled him down this path. We explore what this $100,000 goal meant for Eric, how it propelled him on his entrepreneurial journey, the key learnings he had from each venture, going without a mentor, proving naysayers at his financial job wrong, and the financial roller coaster of building Planswell. I mean, will you rack up $250K in personal credit card debt to not miss your own team's payroll? Eric has focused on creating a transparent company where he values inclusivity for his people as we discuss not only his journey but philosophy on creating a company for his people.

Join in for a conversation with Nadeem Nathoo, Co-Founder and Executive Director at TKS (The Knowledge Society). The Knowledge Society is an education company that works with 13-17 year-olds to mine human potential to make unicorn people. From cold-emailing his way into an internship with, Nobel Peace Prize winner, Muhammad Yunnus' Grameen Bank at 19, to being part of the first cohort of the Next 36, traveling throughout Africa at a young age, entrepreneurship and social impact was a major part of Nadeem's growth. After working as a consultant at McKinsey, Nadeem plunged into the world of entrepreneurship by joining up with his brother in San Francisco. It would be a hypothetical question of what they would do with $10 billion that propelled the creation of TKS back in their hometown, Calgary. Nadeem and his brother created a company that combined their love for learning and exponential technology and it's a journey I've had a lot of fun learning about.

Join in for a conversation with Rob Catalano, Co-Founder and CEO (Chief Engagement Officer) at WorkTango. WorkTango is an HR software company based out of Toronto with a passion to improve work lives. Rob started out his career in the world of traditional marketing for consumer goods and quickly got interested in what drove human behaviour. He became one of the early employees at Achievers, the employee rewards program. This was not the master plan. Rob had left the marketing world to start his next venture but it was a fateful application to a bootstrapped startup he didn't know about that propelled a 10-year career into the world of HR and changing workplaces. After Achievers was acquired Rob had the choice of staying on as a C-suite executive with a very cushy compensation package but he left it to pursue his passion. He left Achievers with his co-founder to bootstrap WorkTango and it's been a 4-year journey of building a company with a passion, not a mission. We cover Rob's various inflection points in his journey, making tough but obvious decisions, and following a passion.

It's been 52 episodes. That's 52 new conversations with 51 different guests (one of the 52 was my first solo episode on my journey). This is another solo episode where I talk about what I've learned in the year of building Accounted For. I cover the challenges in the early days, philosophy on moonlighting, handling advice, art of questioning, plans never working out, surviving, the future of Accounted For and more.

Join in for a conversation with Ben Tam, Founder and CEO of Rizound. Ben has been on his entrepreneurial journey for the last 7 years and he's on a mission to help each child get a PhD level education. Ben's passion for human development and education started from his childhood in Singapore. His original plan to make an impact through politics changed from his time at UBC where he studied political science and philosophy. This pushed him into an entrepreneurial journey in the financial market to start a quant fund, then moved into neuroscience, affordable housing and measuring emotions with facial data with Rizound. Our conversation touch upon various pivots and turns in Ben's wide ranging journey and interesting would be an understatement to the path he has taken.

Join in for a conversation with Cyrus Moradian, CEO and Co-Founder of Wize. Wize is an exam test prep platform based out of Vancouver that services universities throughout Canada and the US. He bootstrapped his first company, Beat Your Course and the precursor to Wize, to help university students based on his own experience as a 1st-year student who struggled in university despite having all-star grades in high school. To Cyrus, going to university was a contrarian move as he comes from a house of entrepreneurs from his parents to his siblings and he is the only member of his family who has pursued post-secondary education. Needless to say, unlike his fellow finance majors who went into fields like investment banking, Cyrus went straight into entrepreneurship out of university. In our chat, we look into when it is time to go from a bootstrapped company to one that fundraises, what Cyrus believes is required to be an entrepreneur for 7 years and how he has thought about building a team where no one has left and much more!

Join in for a conversation with Drew Green, CEO of Indochino. Indochino is a Vancouver based bespoke suit company and it's actually where yours truly got his first bespoke suit as well! But enough about me. So how does one become the CEO of a fast-growing suit company? Well, Drew started his journey as a kinesiology student with a love for basketball. He immediately took an entrepreneurial path to starting a personal training business which he later sold to travel the world and enter into the world of technology companies. A material influence to Drew's unique career journey has been Paulo Coelho's The Alchemist, a fiction book like no other. I personally love this book as well and we go through the various elements of the book that influenced Drew on his journey and his current philosophies on business and life. Though this was a short interview we try to traverse through the very windy journey Drew went through from his athletic years to technology, his current focus with Indochino and more.

Join in for another anonymous episode. I experimented with a number of anonymous episodes in the past where I get someone in various professions like hedge funds, management consulting and we sit down to have candid conversations with what these people actually do. Today is about infrastructure investing. It's a field I've personally had a brief exposure to but it's also a place I've been recommending people look into if they like investing but want something with low volatility and a career that is excel and data-heavy for the meticulous folk. My surface-level knowledge was that infrastructure investing was all about investing in hospitals and solar panels. But we go deep into how that works, what you would do most of the day and more about what this field is like.

Join in for a conversation with Sam Restagno, Managing Director at Golden Spruce Capital, a private investment company that focuses on buying small businesses with an EBITDA of 1-5MM. In our chat Sam takes me through how he persevered through to get into investment banking, and the process of making the decision to leave the plush expense account and comfy banking world to ultimately start a 2 person fund with his business partner. We go through the world of small company investing, the importance of relationship building, the opportunity size, the various funding options and the frugality and hustle you need as founders. I personally got a lot of value out of this chat and even if you aren't someone who isn't hell-bent on running your own investment company in the future I think you'll be able to extract lot's of value out of my chat with Sam. Hope you enjoy.

Join in for a conversation with Armin Yassaie, co-owner of Mos Mos Coffee. Armin takes us into the competitive world of "third wave" coffee shops and we dive into the depths of what it takes to operate and grow a coffee franchise. We also explore the mental model for starting your own coffee shop and explore how Armin's experience from a family construction business played a factor to his jump to the world of coffee.

Join in for a conversation with Marie Chevrier, Founder and CEO of Sampler. Sampler is a Toronto-based startup on a mission to transform the way consumer packaged goods companies distribute product samples. Starting from creating her own idol competition in school to an OG hustler grandmother, Marie had planted the seeds to be an entrepreneur early. However, it would be at the crossroads of forgoing her London MBA and joining an incubator from a single cold email that would take her down the road to seven years in the startup world. Like many mission-driven entrepreneurs, Marie saw a problem that many CPG companies faced from her advertising days and she had found a way to transition that to what is Sampler today. But what many don't think about is the sudden move to New York, the sketchy apartment outside Harlem, the consulting days as she sketched and pitched the ideas for Sampler and the various ups and downs Marie had to persevere through to build a company focused on honesty.

Join in for a conversation with David Cairns, VP of Office Leasing at CBRE Canada and Co-Founder of CBRE Forward. CBRE is a commercial real estate service company and with my own limited experience of commercial real estate, David thankfully creates a picture of the real estate value chain for me early in the podcast. Prior to his successful real estate career, David was a professional poker player. Having been raised by a single-parent household with an entrepreneurial father, David learned to be an independent competitor early. This transpired from being a competitive skier to the competitive world of poker where he earned $200K+ while in university. We explore the 16 hour daily grinds that people don't see on TV, the emotional roller coaster that resembles a venture capital career on steroids and how this experience prepared David to rise from an administrative position to a successful VP in real estate and an intrapreneur.

Join in for a conversation with Marc Champagne, Co-Founder of Kyo. Kyo is a wellness company based in Toronto. It's currently an app that provides prompts to help you with your mental fitness, a simple way I think about it is as a live, digital journal. Marc also has a podcast called Kyo Conversations where he and his guest explore the impact of mental fitness in their lives. I'm a big believer in the mind and body connection and just as much as I'm obsessed with my powerlifting training I am also obsessed with my mental training as well. So needless to say, I was very excited to chat with Marc. You might wonder whether Marc's career started in a spiritual field but it actually started in the world of pharmaceutical drugs. After a decade in the big pharma industry, Marc decided to take the leap with his brother-in-law to "scratch his own itch" by transforming his own 10 years of journaling practices into Kyo. Turns out, being a product manager of mental health drugs can prepare you well to be an app launching entrepreneur as Kyo continues to be a globally ranked top app with influencer content from people like Kevin Rose and Leo Babauta. This was a fun and exciting conversation into Marc's journey of creating a wellness company and I came out of it with personal mindfulness practices for myself and some more perspectives.

Join in for a conversation with Norm Cappell, Co-Founder of Savvyy. Savvyy is a fintech company based in Toronto that is building a digital lending platform. So how does one go from studying English literature to Harvard Law School, capital markets law, investment banking and to building a fintech company? Well, if it includes losing out on a law job in San Fran because of the bursting of the dot com bubble, losing a job in investment banking because of 9/11, breaking into investment banking again only at the top of the real estate bubble to then take a 80% pay cut to join a fintech startup then this is the story you want to hear. Norm has had a fascinating career journey and we go deeper into the world of debt finance and corporate law to educate my own limited knowledge of the realm. It's a journey that spans multiple countries, career fields and economic events and one I hope you enjoy.

Join in for a conversation with Marcus Rader, Co-Founder and CEO of Hostaway. Hostaway is a global property management software company and it's no surprise that this podcast focuses on Marcus' global career and Finnish background. In our conversation we start with epilepsy killing a dream to be a pilot, to running his own loan business at age 11 and the various trials and tribulations of a decade long career in the startup world that eventually led to the creation of Hostaway. We also talk in-depth into various cultural nuances, especially the difference between Finland and Canada. I for one had no idea what it meant to culturally embrace honesty until I spoke with Marcus and also came away with some new found knowledge I hope to utilize in my future visit to Finland.

Join in for a conversation with Stephen Shedletzky, Head of Brand Experience and Igniter at Simon Sinek. If that name is familiar with you it may be because you may have watched Simon Sinek's famous TedTalk or read his first book "Start with Why". Stephen joined Simon Sinek's company, called after his own name, as the 4th employee 7.5 years ago. Stephen's journey to help people feel more fulfilled and engaged by the work they do started when on his first day on his first job at Suncor's leadership program when they fired 1000 people post-merger. This propelled him on a journey to find how he could do his life's work. We chat about the fruitful departure from Suncor, his foray into human capital consulting, why his tenure there was even shorter than at Suncor, starting his own platform for change as a personal 2-year MBA, the 5 paragraph email that got him a call with Simon Sinek and how his journey with Simon started a new chapter in his life. My first meeting with Stephen was when he graciously invited me to attend a talk he was giving at an incubator and though that was a treat it was nothing compared to the intensely fun discussion I got to have with him on the podcast. It was a super fun conversation and we also spoke about maybe even doing a part two in the near future so if you liked it please let me know on my sites contact page.

Join in for a conversation with Sagar Malhi, Co-Founder of Switchboard. Talk about a flashback to the past! Sagar and I went to high school together and re-connected for the first time in nine years last Christmas. Sagar and the Switchboard team had just been admitted to the esteem start-up incubator, Y-combinator, and he connected in Toronto after his three months in San Francisco to dive through his journey. Sagar's entrepreneurial journey started right after university after working in top tech firms like Apple, Intel and Blackberry. We talk about the role of a hardware vs. software engineer, the decision to not pursue a lucrative career in the big tech firms, his short romance for wall street's quant trading world and the trials and tribulations of building a start-up pre and post Y-Combinator.

Join in for a conversation with Marlon Rodrigues, Head of Product at Flexday. If you heard Justin Raymond, Founder of Flexday on episode 19 then you'll be very familiar with the company. If you haven't, then fret not as this is about Marlon's unique journey and we give an overview of the company here too. Marlon's journey traverses through the world of marketing, business development and product throughout a decade in Toronto's start up ecosystem. But, we start earlier to how he delayed graduation to explore accounting then to operating a hostel in a remote region of Peru without knowing a word of Spanish. This became an inflection point that catapulted Marlon into the start up world but this was still a 10 year journey of him following his curiosity and embracing the uncertainty and the feeling of not knowing exactly what he wanted to do. It's a feeling I know all too well and one I think everyone experiences but is afraid to be okay with. Maybe after hearing Marlon's story you will change your mind or if you're going through it now, maybe you'll feel the comfort I felt.

Join in for a conversation with Megan Tong, the Co-founder of Kanga Aussie Meat Pies. If you don't know what a Australian meat pie is I suggest you Google it and immediately eat one. If you're a Toronto listener you're in luck because Kanga's Aussie Meat Pies is based out of Toronto and they are awesome. Megan started her journey as an accountant. Though she found her way to her passion of microfinance early, she left it all to take on the entrepreneur's journey of opening a restaurant. I've been a big fan of Kanga long before I knew Megan and our chat goes through the full story of how she started the company, operated it and to selling it. We also touch upon how Kanga is not how she "retired" but was actually through her side hustle to her entrepreneurship: real estate. This was a very insightful conversation into the restaurant business and how to just focus on having fun.

Join in for a conversation with Larry Lau, the Founder of Eighty8 Ventures. Eighty8 Ventures is a venture studio in Toronto and London that helps entrepreneurs build digital products with the help of an in-house development team. Though he runs a venture studio that develops technical products, Larry started out as an entrepreneur in digital marketing. His foray in entrepreneurship began with building a globally ranked top Pokemon community site that later got acquired by IGN. Yet, he didn't pursue his next venture till much later after graduating after nearly getting kicked out of university with a medical science dream left in the past. Since then, he built a marketing agency became of an angel investor and venture founder who is focused on helping startups and creating brands. This was an extremely fun episode and given how gangster this guy is, we weren't able to cover his full story so I may have to have him come on again in the near future but until then please enjoy my fun chat with Larry Lau.