40 episodes

Why are entrepreneurs driven to do what they do? Put in endless hours and endure countless failures in pursuit of their dreams. Ilan Jacobson is one of those entrepreneurs. He's built businesses in sectors ranging from finance to axe-throwing. He's endured his share of failures, but he, and the entrepreneurs he interviews each week, wouldn't go down any other path. Hear their stories: how they conceived of their ideas, cleared hurdles, endured failure, and ultimately, achieved success, on A Dealmaker's DNA with Ilan Jacobson.

A Dealmaker's DNA with Ilan Jacobson Ilan Jacobson

    • Business

Why are entrepreneurs driven to do what they do? Put in endless hours and endure countless failures in pursuit of their dreams. Ilan Jacobson is one of those entrepreneurs. He's built businesses in sectors ranging from finance to axe-throwing. He's endured his share of failures, but he, and the entrepreneurs he interviews each week, wouldn't go down any other path. Hear their stories: how they conceived of their ideas, cleared hurdles, endured failure, and ultimately, achieved success, on A Dealmaker's DNA with Ilan Jacobson.

    Episode 39: Jamie Opalchuk

    Episode 39: Jamie Opalchuk

    What goes into creating a company culture? How do you foster a community of mentorship within your company? These are some of the questions that today’s guest will address in this conversation.
     
    Jamie Opalchuk is the Founder and CEO of HostPapa. In today’s episode, you’ll learn more about how he got there and what he thinks about building and running a company today. Listen to the episode to hear Jamie speak about his first entrepreneurial experience as a lemonade stand owner, how COVID has changed watercooler talk and after-hours networking, and how he views failure.
     
    Topics Discussed in This Episode
     

    Why Jamie started HostPapa originally and what his goals were
    What life was like for Jamie growing up
    Whether it’s upbringing or genetic makeup that makes people act on their ideas
    How Jamie’s upbringing makes him less risk-averse
    What’s happening as watercooler talk and other networking becomes rarer
    The time between the lemonade stand and HostPapa
    How Jamie views failure
    Whether failure should be an option
    What Jamie has learned about scaling
    Creating a company culture
    Scaling mentorship within a country
    Jamie’s continuous learning habits
    The importance of routine

     
    Related Links
     
    Jamie Opalchuk
    HostPapa
     
    Quotes From the Show
     
    “I had a couple other businesses, and I decided to solve my time constraints, I would start another business.”
     
    “Great companies are built on people and ideas and vision, and then execution.” 
     
    “When I was in school, procrastination was a habit.” 
     
    “Small steps lead into big marches” 

    • 31 min
    Episode 38: Jay Rosenthal

    Episode 38: Jay Rosenthal

    How does someone find their way from working in politics and policy into the cannabis field? Today’s guest is Jay Rosenthal, and his interesting work history has taken him from the political field to entrepreneurship and now into the cannabis industry. Listen in to hear Jay’s thoughts about what sparked him to go into entrepreneurship, what Canadian businesses can learn from American businesses, and what characteristics you need to succeed in the cannabis industry.
     
    Topics Discussed in This Episode
     

    Jay’s origination story
    What was in Jay’s background that led him to his career path
    What brought out Jay’s entrepreneurial spark
    Jay’s thoughts on the mentality that an entrepreneur has to have
    What Canadians can learn from the way Americans do business
    How it took so long to legalize cannabis
    How the War on Drugs camouflaged racism
    Where to double down if you’re interested in becoming a cannabis entrepreneur
    The next domino after cannabis to fall
    What characteristics you need to succeed in the cannabis industry
    Why entrepreneurs should get involved in politics

     
    Related Links
     
    Jay Rosenthal
    Business of Cannabis
     
    Quotes From the Show
     
    “The arc needs to be having it work. There’s going to be hiccups along the way, because not everything works especially when you’re building something new.”
     
    “When I got into politics or working for elected officials, it didn’t seem like a stretch.” 
     
    “The war on drugs in the US – and to a lesser extent here – it really only put black and brown people behind bars in the US.”
     
    “I just don’t see where you would be able to go into a store and buy mushrooms.”

    • 33 min
    Episode 37: Tom Short

    Episode 37: Tom Short

    Tom Short is the founder and Chief Customer Officer at Kudos, a company that helps improve company culture and engagement with employees and colleagues. Company culture is an important requirement for today’s job seekers, so if you want a company to succeed, it’s important to learn how to create a good company culture. And according to Tom, even if your company culture is bad currently, it’s not too late to make a change. Listen in to hear what Tom has to say about how he found this path, what’s involved in changing culture, and how to show appreciation in a way that’s authentic.
     
    Topics Discussed in This Episode
     

    What Kudos is for
    Tom’s childhood and how he found his path
    Tom’s opinion on naivete
    How much of Tom’s trajectory was up to DNA
    How coming from a military family influenced Tom’s path
    How hard it is to change a company’s culture
    How to do due diligence on a company’s culture
    Why companies choose not to invest in culture
    How to appreciate in an authentic way
    How to train people to be better colleagues when it’s not naturally part of their demeanor
    How much culture comes from stereotypes
    How to reach Tom

     
    Related Links
     
    Tom Short
     
    Quotes From the Show
     
    “Lots of people have great ideas and epiphanies in the shower or they see opportunities, but it’s all about getting after it and making it happen.” 
     
    “Every business on the planet has got people, and people are weird"
     
    “Everyone’s lousy at whatever they start at the first time.”

    Episode 36: Delee Fromm

    Episode 36: Delee Fromm

    How can you follow your passions in life? What role does emotional intelligence have on your ability to negotiate and make deals? Delee Fromm has answers for some of these questions. Delee is a lawyer with a background in psychology who currently works as a speaker and author. Listen to her interview to hear what Deele has to say about how she grew up, what she thinks people do wrong in negotiations, what men and women do differently in terms of dealmaking, and how to reduce inequality.
     
    Topics Discussed in This Episode
     

    Delee’s background
    What the effect is of growing up in small towns
    What Delee’s parents did right and wrong
    How you follow your passions
    What Delee learned about human nature in her psychology background
    Whether intelligence is innate or learned
    Key components of emotional intelligence
    The emotional responses of psychopaths
    What people do wrong in negotiations
    Whether men and women negotiate differently
    Doing better at eliminating inequality
    Equality of outcome versus equality of opportunity
    What companies and organizations can do to support diversity
    How to balance diversification with virtue signaling

     
    Related Links
     
    Delee Fromm
     
    Quotes From the Show
     
    “You feel unique when you’re in a small setting.” 
     
    “I’m a person who believes that you follow your bliss.” 
     
    “Because they’re not aware of the emotion bubbling up, it becomes very strong, and they may act on it before they’re aware.” 

    Episode 35: Matt Cohen

    Episode 35: Matt Cohen

    Matt Cohen was highly influenced by his first investment in Turnstyle Solutions, and he used what he learned as he became the founder and managing partner at Ripple. In today’s interview, Matt shares useful information about his experiences in investing, founding, and entrepreneurship. Listen to the episode to hear what Matt has to say about what creates entrepreneurs, the necessity of sacrifice as an entrepreneur, and the importance of maintaining a good network.
     
    Topics Discussed in This Episode
     

    What Ripple is and why Matt started it
    What creates entrepreneurs
    Matt’s backstory
    The level of sacrifice involved in being an entrepreneur
    Matt’s view on failure
    Matt’s curiosity
    Maintaining a good network
    The line between business and personal
    Matt’s mentors
    How to pick jockeys
    How our minds perform at a high level
    How to reach Matt

     
    Related Links
     
    Matt Cohen
     
    Quotes From the Show
     
    “Building out a network beyond what you grow up in, in the bubble you grow up in, is really important.” 
     
    “What I was very adamant about doing as soon as I left high school was trying to get out of the bubble I grew up in.” 
     
    “You don’t want someone who has gone through failure and is just glass half-full person their entire life.” 
     
    “When you ask for advice, you get money, and when you ask for money, you get advice.”

    • 39 min
    Episode 34: Adam Levinter

    Episode 34: Adam Levinter

    Did you know you can still succeed as an entrepreneur even if you’re not certain about your path? Even if you struggle with stress and anxiety? These are some of the issues that today’s guest is going to talk about. Adam Levinter is the founder and CEO of ScriberBase, a published author, and a podcast host. Listen to the episode to hear what he has to say about why too much self-imposed pressure is detrimental, why asking for help makes you stronger, and what’s happening in the world of subscription-based business models.
     
    Topics Discussed in This Episode
     

    How Adam got to the space he’s in
    Whether going into business for himself was something that was on Adam’s mind from childhood
    Adam’s advice to people who think they need to have a defined path
    Why too much pressure is detrimental
    Techniques that Adam finds to be effective in dealing with anxiety and stress
    Self-awareness and asking for help
    Building trust as a salesperson
    What ScriberBase does
    Areas where Adam thinks that there’s going to be a boom
    What some subscription businesses get wrong
    Whether the excitement of subscription models is going to change
    What Adam wishes he would have known early on

     
    Related Links
     
    Adam Levinter
     
    Quotes From the Show
     
    “I feel like this chapter is a chapter of many in this life.” 
     
    “When I feel a sense of anxiety, or I feel a sense of stress, I get to a pen and paper as fast as I can.” 
     
    “Nobody cares about your idea and how good it is. Will people whip out their wallets and pay for it?” 

    • 43 min

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