James Benham is a bootstrapped serial entrepreneur, corporate innovator, and investor focused on technology that transforms the world’s oldest industries. He is the Co-Founder and CEO of JBKnowledge, a multinational technology and consulting company founded in 2001 that develops industry-leading software for the largest insurance companies across the globe. He is also the Co-Founder of two insurance tech products: SmartCompliance and Terra.

Prior to being focused solely on insurance, James built multiple technology products for the construction industry. His most successful, SmartBid, became the leading construction bidding software for general contractors worldwide, culminating in a multi-million dollar acquisition in 2018. With over 9,500 followers on LinkedIn, James is a sought-after consultant and speaker at the forefront of innovation, technology, sales, and business leadership. He is the host of The InsureTech Geek Podcast and has spoken at over 400 conferences in the last 15 years. His first book, Be Your Own VC: 10 Bootstrapping Principles to Generate Cash and Keep Control, is set to release this fall.

James's first book: Be Your Own VC: 10 Bootstrapping Principles to Generate Cash and Keep Control, is set to release this Fall.

In this episode we talked about the pain vs. control, entrepreneurship, persisting through overwhelming fear, compassionate leadership, the power of checklists, and the discipline and focus it takes to land planes—metaphorically, and literally.

Connect with James here:

Website: https://jamesbenham.com/
LinkedIn: https://www.linkedin.com/in/jbenham/
Twitter: @jamesmbenham
Instagram: @jamesmbenham

Courtney Watts is a human-centred design strategist at CGI, bringing human-centred systems thinking and mindfulness together to help design teams and global enterprises alike solve complex problems. She completed her masters in international business at Hult International Business School in 2014, splitting her time in the program between Cambridge, and Shanghai. She's spent most of the last 8 years in global IT consulting enterprises and startups, including a glorious few years in Toronto. She returned to her hometown of Pittsburgh, Pennsylvania, and joined CGI back in October 2020. In addition to her work at CGI, she works with students at Carnegie Mellon University.

The universe truly aligned for this conversation to take place. In this conversation, Courtney and Hamza talk about the love of language. They pick apart the concept of love and how that relates to fear. Are you team love or team fear? They talked about identity, the importance of healing and mindfulness at work. Courtney and Hamza touched upon things like stress and burnout and the importance of creating human-centred systems. With notes on Formula 1 racing and spirituality, it was a conversation everyone should hear at least once!

Connect with Courtney here:

LinkedIn: https://www.linkedin.com/in/wattscourtney/

Hamza Khan is a Democratic Strategist & political activist based in the Washington Metro Region's Maryland suburbs. He is also a frequent guest on national & international news stations to provide analysis & commentary on topics ranging from the environment to immigration & developing markets. Hamza is the founder of The Pluralism Project, an organization working to empower everyday Americans hailing from diverse narratives in our political process. He has previously consulted members of Congress & the US Senate on outreach strategies to immigrant populations & minority voters. He is a keynote speaker who has spoken at dozens of social & political events across the country. Hamza also has a background in speech-writing, with clients including ambassadors, political candidates, religious leaders & Fortune 500 executives.

In this conversation, Hamza Khan and Hamza Khan discussed how their path crossed and what it is like to share the same name. They talked about an array of subjects such as Ms.Marvel, social justice, South-Asain identities, burnout, and believe it or not,  infiltrating FoxNews. Ultimately ending on a very poignant note about the importance of creating empathy and how your life can change, just one breakfast at a time.

Follow Hamza here:

Instagram: https://www.instagram.com/hamzapolitics/
Twitter: https://twitter.com/hamzaskhan
Newsletter: https://www.hamzakhan.me/subscribe
More: https://linktr.ee/HamzaSKhan

Herbert Lui is an editorial director and author. He has been writing since he was 15. His work has appeared in publications like Fast Company, Hypebeast, and Quartz, and he later joined Lifehacker as a staff writer. His company Wonder Shuttle has advised teams at organizations such as the City of Toronto, Shopify, and Skillshare on their writing and publications.

In this conversation, went deep into his latest book, Creative Doing and the impact it has had on both our journeys since the last time we spoke on the podcast. We also talked about generational trauma, death anxiety and what it means to have a “purpose” in life. It also wouldn’t be a conversation with Herbert if there wasn’t a little Kanye West in there as well.

Follow Herbert here:

Blog: https://herbertlui.net/
Newsletter: https://herbertlui.net/best-of-books
Twitter: https://twitter.com/herbertlui
Medium: https://herbertlui.medium.com/
LinkedIn: https://www.linkedin.com/in/herbertlui

Earlier this year, I had the immense privilege of delivering a convocation address to the 2019 graduates of the University of Toronto Scarborough (UTSC) in Toronto, Ontario.  Inspired by The Toronto Raptors' crowning as 2019 NBA Champions, I urged graduates to contend with imposter syndrome and talk themselves into greatness. Here's the full audio for your listening pleasure. Links to the video and transcript are below.

Remember: Be great. Talk yourself into it.

FULL VIDEO: http://bit.ly/2J2eMme
FULL TRANSCRIPT: http://bit.ly/2x9gXze

David Ip Yam is the Project Director of Student Service Excellence at York University. He’s also the Co-Founder of Relationship Zen. By day, he’s an award-winning higher education practitioner and scholar with 10+ years of actively learning, facilitating, an co-creating personal, community, and professional mastery. And by night, he’s a martial artist and relationship strategist. He’s in many ways the perfect synthesis of all of the themes we’ve covered in the show thus far: multi-potentiality, self-awareness, confidence, perseverance, resilience, and discipline.

In this conversation we talked about being intentional in relationships, the hidden power of martial arts, and cultivating a beginner’s mindset. We also talked about knowing when to stop, managing energy to adequately show up, and staying locked on the end goal.

It was the perfect conversation to end this season, and I’m so glad you’re here for it.

NOTE: I know, I know—the audio quality for our last three intros is awful. Kwaku and I are working on a fix and will announce on the @iia_podcast Twitter account once it's been fixed. Thanks for your patience!

Blair Smith is a Professor of Marketing and Digital Media at George Brown College. He’s also a Learning Experience Designer and Instructor at the Canadian Marketing Association. On the MBTI, he registers as an INTP—a combination found in only 3% of the population. What does this mean? He’s an ingenious problem solver, an innovation architect, and “the secret weapon”. Over his storied career, spanning across Robert Half International, General Mills Canada, Evergreen Canada, and more, Blair has won awards for mentoring, marketing innovation, and content marketing. His goal is to cut through the buzzwords, clickbait, jargon, and endless stream of tactics and tools to demystify marketing and digital media at its fundamental parts.

In this conversation we talked about social media: the good, the bad, and the ugly. We also talked about slow and deep thinking, the importance of family, and rules for what goes into your calendar and what doesn’t.

Adam Rodricks is the Senior Manager of Social Media & Community at KPMG. His claim to fame in the world of social media and blogging came in 2007 when he reluctantly sold his blog after being served with a cease and desist. The important takeaway from the ordeal was validation: he could make an impact (and a career) through engaging conversation. Adam is a 2-time “Top 30 Under 30 Canadian Blogger to Watch” and a previous winner of the National Rogers Marketing Competition, for which he also held the title of best undergraduate speaker in Canada. He’s spent the last decade growing the social properties of Canada's most prominent brands, managing all aspects of their digital marketing strategy including social listening, management of social media channels, crisis comms and social media programs. His work as a social media influencer has been featured on CBC, CTV, Yahoo, BNN, DigitalJournal.com, MaximumPC, WhatCulture.com, staples.com, and nintendo.ca

In this conversation we talked about the power of social media, the state of the internet, and rebounding from failure. We also talked about balancing your time, the importance of exercise, and having multiple focal points.

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NOTE: Unfortunately we've been having some audio issues. As such, the intro is a little hard to hear (and we're going to fix that as soon as we can). However, the actual episode sounds great! Also, we recorded this episode during the NBA Playoffs—enjoy our optimistic predictions for our beloved Toronto Raptors!

Megan Ramwa is the Founder & CEO of Sonder Toronto. Her desire to create “something bigger than herself” has always been at the forefront of her career. Megan graduated from the Law and Business program at Ryerson University. Shortly after graduating, she became a marketing and communications professional at a top Bay Street law firm where she was involved in many strategic initiatives such as the Canada 150 campaign and launching the firm’s first Instagram account. While juggling her 9-5, Megan continued to exercise her creativity on theawkwardadult.com - a personal blog that explored what it meant to be a young adult. In addition, Megan has launched a fashion and sustainable-tech company (Sonder Toronto), and has collaborated with local entrepreneurs to produce content. Megan is also involved with the Martin Family Initiative as a mentor to Indigenous high school students and was a marketing advisor to FLOCK - a project focused on providing women with the resources and support to explore entrepreneurship.

In this episode we talked about disrupting fashion, balancing full time work and entrepreneurship, and finding deeper meaning in your work. We also talked about immigrant parents, avoiding burnout, and dealing with failure. It was a fun and easy conversation that covered a lot of ground.
 

Joining me as a co-host today is Megan’s business partner, Aishah Shihabdeen.

Sheliza Jamal is an educator, speaker, and equity and inclusion coach. She is a graduate of the Harvard Graduate School of Education where she studied the impact of arts in education, leadership in social change organizations, education entrepreneurship innovation, and educational policy through the lens of systemic inequities. Sheliza also holds an Honors BA in Theatre and BEd from York University and is starting her PhD at OISE, University of Toronto in the Department of Social Justice Education. Sheliza brings over a decade of experience in public education teaching and designing and implementing programs and services aimed at addressing inequitable outcomes for underserved communities. Sheliza has a background in theatre performance and education and often uses theatre-based techniques to develop a sense of embodied empathy and engage participants in dialogue about oppression. Sheliza is an Ontario Certified Teacher (OCT) and a K-12 Inclusion Learning Coach with the Toronto District School Board where she supports students, teachers and leaders in programs that foster equity and inclusion to meet the needs of diverse learners.

In this conversation we talked about building confidence, managing imposter syndrome, and unconscious bias. We also talked about equity, diversity and inclusion, casual racism, and the negative effects of social media.