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Jordan Nahmias shares his journey from law school to lawyer to know coaching others on how to change careers at Unstuck Consulting. He discusses his dissatisfaction with his law career and the moment he realized he needed a change. Jordan talks about the fear and terror he experienced when deciding to leave his law practice and the support he received from his family and friends during his career transition from being a lawyer to becoming a coach and therapist. He shares his passion for helping people and his ability to listen and understand others.
About Jordan Nahmias:Jordan Nahmias is Founder and Principal at Unstuck Consulting Inc. At Unstuck Consulting, he helps lawyers and other professionals find purpose in their careers through coaching.
Before starting Unstuck, Jordan was a lawyer working at Goldenberg Nahmias LLP, Hall Webber LLP, and his own law firm, Nahmias Law Professional Corporation.
Jordan studied law at the University of Toronto and the University of Hong Kong, earning his Juris Doctor in 2008. He also has a B.A. in Philosophy from Huron University.
In this episode, we discuss:
(01:34) - Jordan’s journey growing up and his early career path
(03:49) - His time after law school teaching yoga and doing legal work on the side
(04:29) - Starting his own legal practice and focuses on film and TV work, growing the practice, and merging with another firm
(05:19) - The decision to leave legal practice in 2021
(06:30) - Reflecting on dissatisfaction with the legal profession from the beginning
(08:52) - Realization that a drastic change in career was needed.
(09:13) - COVID and having a child as critical factors that sped up the decision to leave law
(10:00) - Impact of not bringing the best self home to the family
(12:39) - Hitting the "wall" in a career similar to the scene in "The Truman Show"
(14:43) - Feelings of terror and preparation involved in making a career change
(16:45) - Fear of failure and responsibility in making the decision to change careers
(18:15) - The privilege of being able to make such a change and the importance of a supportive network
(20:47) - Feedback received during the transition and the importance of accepting one's feelings
(24:11) - Explanation of the new career path in helping others navigate periods of stuckness
(27:18) - Working with clients to help them navigate career changes and find satisfaction
(30:51) - Insights from the keynote on doing scary things and the importance of facing fears
(32:39) - Dealing with regret by practicing gratitude
(34:13) - Emphasis on focusing on feelings and the person rather than rushing to solutions
(39:10) - The role of habits and practices in helping people manage their careers and personal lives
(41:13) - Using social media to connect with others and shared experiences
(42:40) - What’s next for his career and how people can get in touch with him
Fast Favorites:
* 🎙- Favorite Podcast: Making Sense by Sam Harris
* 📰- Favorite Newsletter / Blog: The Imperfectionist by Oliver Burkeman
* 📲- Favorite Tech Gadget: Teleprompter setup with an SLR and iPad for Zoom calls
* 📈-  Favorite New Trend: Baggy clothing coming back into style and the acceptance of discussing dissatisfaction with work, especially for men
* 📚- Favorite Book: Fiction: American Psycho; Non-fiction: Let Your Life Speak by Parker Palmer and The Middle Passage by James Hollis
* 🤔 - Favorite Life Lesson: "No mud, no lotus" and Nothing is permanent: good times and bad times both pass
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This week in the Tank we have Winter Mead, founder of Coolwater Capital, to discuss his background in venture capital and the challenges faced by emerging fund managers. He emphasizes the importance of understanding the LP perspective and operationalizing the fund to attract institutional investors. Winter also shares insights from his book on raising a venture capital fund and the mission of Coolwater Capital's Accelerator program. The program aims to bridge the knowledge gap for emerging VCs and provides guidance on fund formation, LP fundraising, and fund management. Winter highlights the criteria for selecting VCs for the program and the focus on community orientation.
The conversation covers three main themes: fund management and operations, fundraising, and the future of venture capital. Winter emphasizes the importance of setting up the operations of a fund correctly, learning the new language of being a fund manager, and understanding the market when it comes to fundraising. He also discusses the benefits of building a network and leveraging relationships in the venture capital industry. Winter shares their thoughts on the future of venture capital, including the potential for consolidation, the role of AI in fund management, and the continued focus on investing in big themes and challenges.
And John Ruffolo and Matt Cohen discuss the week’s news.
About Winter Mead:Winter Mead is the founder and managing member of the investment firm Coolwater Capital. The firm focuses on emerging managers and technology investments. He is author of How To Raise A Venture Capital Fund, and operates Coolwater, an academy for training, building and scaling emerging managers. Coolwater has worked with over 240 emerging managers in the last four years.
Prior, Winter helped build and invest an evergreen fund at SAP, a publicly listed enterprise software company, where he co-founded the LP transparency movement called #OpenLP. Winter also worked as a private equity and venture capital investor at a large multi-family office in San Francisco. Winter has completed seventy-nine institutional investments, as well as over twenty-five other investments since leaving his institutional allocator role. He served as junior faculty at Stanford Graduate School of Business on Venture Capital and Entrepreneurship.
Winter holds a Master of Science degree majoring in Management Research from the University of Oxford and a Bachelor of Arts degree from Harvard University.
In this episode, we discuss:
(02:06) John Ruffolo discusses the potential political motivations behind not including a higher capital gains tax in the recent budget proposal and how it might be a strategic move by the government to pressure the conservative opposition
(02:29) A potential second reason for the omission might be a need for more time to draft detailed rules around the new capital gains strategies, suggesting it's still a work in progress
(03:35) The governmental challenges in managing the budget and public expectations, highlighting the difficulty in aligning political strategies with economic needs.
(06:01) Concerns about the impact of unrestricted immigration on housing markets, criticizing the government for not addressing the core issues of housing supply.
(07:34) The need for national unity and economic growth rather than redistributive measures that pit different societal groups against each other.
(12:40) Llama 3 might cause disruption in the AI model market, praising its rapid adoption and potential to democratize high-quality AI tools
(16:34) Winter Mead describes the mission of Coolwater Capital as supporting emerging managers, detailing how the firm aids them through training and network building to establish and grow their funds.
(17:24) Foundational experiences at Sapphire Ventures that led him to focus on venture capital, highlighting the importance of understanding the investment landscape and operational aspects of managing a fund.
(19:39) Discusses the imp

Our focus on the 2024 Canadian Federal budget continues, we have Jon Love Executive Chair and Founder of KingSett Capital back to discuss the lack of emphasis on fostering prosperity and a shrinking GDP per capita.
While the budget offers some incentives aimed at improving housing affordability and encouraging investments in Canada, the increase in capital gains tax and other measures may slow down real estate development.
Notably, the budget doesn't sufficiently tackle the need to boost the housing supply, which is essential for a healthy real estate market. These tax hikes and regulations could also deter investments and lead capital to flee the country. The budget overlooks important challenges faced by small and medium businesses and predominantly focuses on demand without sufficiently addressing supply issues.
In this episode we discuss:
(00:46) - Overview of the 2024 Canadian Federal Budget and its real estate implications
(01:32) - Discussion on new incentives and the overshadowing impact of capital gains increase
(05:12) - Challenges in the condo market and strategies for developers
(09:28) - The misconceptions around financialization in real estate
(13:24) - Necessity for a prosperity agenda and strategies for economic growth
(17:31) - Potential effects of the budget on small and medium businesses
(19:19) - The long-term consequences of current government policies
About Jon Love: Jon Love is the Executive Chair and Founder of KingSett Capital, a prominent private equity real estate investment firm. Since its inception in 2002, KingSett has impressively managed over $17 billion in assets, earning a strong reputation for its effective investment strategies across various sectors, including Growth, Income, Urban Development, Mortgage, Residential Development, and Affordable Housing.
Before his leadership at KingSett, Jon had a distinguished career at Oxford Properties, beginning in 1980 and eventually becoming President in 1987 and then CEO in 1992. He notably guided Oxford's transition to a publicly traded company in 1995. In 2001, Oxford was privatized when it was acquired by the Ontario Municipal Employees Retirement System (OMERS) in a $4 billion deal.
Jon actively participates in prestigious business organizations and has received numerous accolades for his leadership and academic achievements, including an Honorary Doctorate from Western University in 2016, membership in the Order of Canada (C.M.) in 2018, and prestigious awards such as the Ivey Business Leader of the Year Award and the NAIOP Rex Icon Award in 2023.
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This week we're joined by Nicolas Mulroney, President and CEO of Bond Bakery Brands. Nicolas shares his transition from a finance career at RBC to leading a thriving baking enterprise, highlighting the pivot that led him from Bay Street to Bakery Street.
We talk about the founding of Bond Bakery amid the challenges posed by the COVID-19 pandemic and how his upbringing in a political family shaped his entrepreneurial spirit. Nicolas discusses how technology integrates in his business, he offers insights for budding entrepreneurs, and he outlines his future aspirations for the baking industry in Canada.
We are also joined by John Ruffolo to talk more about the proposed Federal budget and other news in tech.
About Nicolas Mulroney:Nicolas Mulroney is the Co-Founder, Chairman, CEO, and President of Bond Bakery Brands Ltd.
Based in Toronto, Ontario, Bond Bakery Brands operates as an investment platform accelerating the growth of bakery companies throughout North America. The company emphasizes community engagement and investment in family- and founder-run businesses, striving to demonstrate that profitability and positive impact can coexist. Bond's portfolio includes a variety of bakery companies, and it employs over 600 individuals across 11 facilities.
Before launching Bond Bakery Brands, Nicolas served as the Chairman of Portofino Bakery from June 2019 to October 2020, and he remains the Founder and Managing Partner at Northern Waters Capital since August 2018. His career in the capital markets sector includes roles at CIBC Capital Markets in Investment Banking and Institutional Equity Sales, and at Park Lawn Corporation as Vice President of Mergers, Acquisitions & Strategic Initiatives.
Nicolas holds an MBA from the University of Toronto's Rotman School of Management and a Bachelor of Arts from Boston College.
In this episode, we discuss:
(01:52) John Ruffolo discusses meeting with Minister Freeland focusing on adverse effects of proposed capital gains changes on entrepreneurs and investors
(03:32) The dual concerns for innovation community: impact on entrepreneurs and availability of capital
(05:00) The federal budget is poor public policy, particularly for venture capital, stressing the importance of maintaining strong domestic capital source
(07:24) The need to grow the economic pie rather than just redistributing income
(13:45) Public discussions should aim at understanding fundamental problems and exploring viable solutions to foster a collaborative environment across various sectors
(15:54) Nicolas Mulroney’s entrepreneurial journey
(16:09) Nic’s upbringing and the influence of his family, especially his father from Prime Minister Brian Mulroney, on his career choices
(18:27) Challenges and learning experiences from his time in finance that prepared him for entrepreneurship
(20:10) Nic’s decision to leave finance to pursue running a business, attracted to transforming old economy industries
(21:20) The process and rationale behind using a search fund to acquire a business, eventually leading to the purchase of a bakery
(23:37) Advice from his father and Paul Demarais, encouraging him to pursue entrepreneurship
(25:33) Operational challenges faced during the pandemic and the strategic shift towards building Bond Bakery Brands
(30:08) Describes expansion of Bond Bakery Brands, highlighting the acquisition of assets and focus on commercial bakeries
(32:08) The use of technology and data to improve operational efficiency across Bond Bakery Brands
(34:36) Consumer trends affecting the bakery industry and the strategic response of Bond Bakery Brands to changing market conditions
Fast Favorites:
* 🎙- Favorite Podcast: How I Built This
* 📰- Favorite Newsletter / Blog: New York Times Dealbook
* 📲- Favorite Tech Gadget: Phone
* 📈-  Favorite New Trend: Ozempic
* 📚- Favorite Book: The Outsiders
* 🤔 - Favorite Life Lesson: It's a funny thing, the more I practice, the luckier I get.

On this week's episode, we welcome John Li, CEO and Co-Founder of VimCal. John shares the rollercoaster of starting VimCal, from the initial struggles to gaining traction through a product-led approach, particularly appealing to like identifying and appealing directly to its most influential users—executive assistants.
Plus, hear about the extreme loyalty VimCal has inspired, including one user's permanent tribute with a VimCal tattoo.
This a candid conversation about resilience, user-focused development, and the importance of customer feedback in building a product that people not only use but love.
Also, we have John Ruffolo to discuss the week’s news. Note the news rundown was recorded before the Federal Budget proposal was released, for a full breakdown of the budget go here.
About John Li:John Li co-founded Vimcal in 2018 and serves as its CEO. Vimcal is a fast calendar app that helps people manage many meetings and was in Y Combinator. It has features like time zone conversion and keyboard shortcuts. The company introduced Vimcal EA for Executive Assistants, saving time for users at companies like Kleiner Perkins and Dropbox.
Before Vimcal, John worked at Twitter as a software engineer from 2016 to 2018, after his company, Peer was bought by Twitter. He started his career with an internship at Apple.
John studied at the University of California, Berkeley, where he earned degrees in Computer Science, Business Administration, and French.
In this episode, we discuss:
(0:02:36) Public reactions to the growth of the public sector and concerns about Canada's economic policies favoring public sector employment over entrepreneurship
(0:04:17) Inefficiency in government and the significant decline in productivity among remote public sector workers
(0:07:34) The upcoming federal budget will lean heavily on tax increases and the mobility of wealthier individuals and the potential for them to leave Canada due to high taxation
(0:15:25) John Li shares his entrepreneurial background, mentioning his early career moves, including working at Twitter and an internship at Apple, which influenced his product development perspective
(0:18:21) The moment he and his co-founder decided to start their venture after realizing they enjoyed working together on technology projects outside their corporate jobs
(0:20:35) The initial concept for their AR startup, aiming to integrate native advertising into AR environments, and how this idea was ultimately too premature for the market
(0:21:51) Pivoting from their initial AR idea during YC after feedback that the market timing was off, describing the emotional challenge of shifting away from an idea that defined their entrepreneurial identity
(0:25:56) The shift to VimCal, born out of the frustrations with scheduling during their fundraising. He emphasizes the importance of building a product that the founders themselves would use
(0:33:48) The enthusiastic reception of VimCal within the YC community and how personal onboarding calls helped refine the product and convert users into paying customers.
(0:43:16) A memorable encounter with a VimCal fan who demonstrated his loyalty through a permanent tattoo of the VimCal logo, highlighting the passionate user base of the product.
(0:56:23) The future focus of VimCal on enhancing team features for both internal and external scheduling, aiming to simplify complex scheduling scenarios and expand team collaboration tools

Fast Favorites:
* 🎙- Favorite Podcast: My First Million
* 📰- Favorite Newsletter / Blog: James Clear
* 📲- Favorite Tech Gadget: Sous Vide
* 📈-  Favorite New Trend: Living At Home Into Your 20s
* 📚- Favorite Book: Animal Farm
* 🤔 - Favorite Life Lesson: Learning how to deal with emotional triggers on a daily basis
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John Ruffolo and Matt Cohen break down the federal budget proposal announced yesterday and its implications for investors, founders, and entrepreneurs.
The increase in the capital gains tax and the lack of appreciation for founders and owners of businesses are driving the narrative of taxing success and the impact this will have on young founders, corporations, and very mobile individuals who can leave the country.
The potential negative knock-on effects this will have on innovation and productivity gains and that damage to the startup ecosystem and investment landscape across Canada. The conversation explores potential next steps and the importance of being a part of the solution.
Follow Matt Cohen and Tank Talks here!
Podcast production support provided by Agentbee.ai


This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit tanktalks.substack.com