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Ever wonder how someone becomes a venture capitalist?

Winter Mead is the founder of Coolwater Capital, the YC for VC funds. He's invested in over 90 funds and has helped launch hundreds of VC firms. Venture operates in circles of trust. Those circles aren’t arbitrary, they’re built over decades. Ecosystems compound relationships the same way companies compound capital.

But the deeper insight is this: VCs are also fundraisers.

Every venture firm answers to limited partners. They raise funds, demonstrate performance, defend strategy, and differentiate in a crowded market. That means every investment is not just a bet on a founder, it’s a bet that must be defensible to institutional capital.

Founders who understand this dynamic immediately gain an edge.

In this episode, we break down how venture capital actually works. If you’re building a company or allocating capital, this conversation will sharpen how you think about incentives, access, and positioning.

What We Cover:

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ABOUT WINTER & COOLWATER

Winter Mead is the Founder and Managing Member of the investment firm Coolwater Capital, which exclusively focuses on emerging managers and technology investments. Coolwater is an academy for training, building and scaling emerging managers, a curated community of VC investors and early-stage investment specialists, and an investment firm. Coolwater has helped launch over 300+ emerging managers in the last four years, establishing strong ties and trust with these managers, who form the foundation of the Coolwater community. Coolwater has made over 90 investments into its accelerator ecosystem supporting the next generation of founder investors and new technologies.

Winter is also the author of "How To Raise A Venture Capital Fund" and an upcoming book, "How To Set Up A Venture Capital Fund." Prior to Coolwater, he played a key role in an evergreen investment fund at SAP and co-founded the LP transparency movement called #OpenLP. Winter's extensive experience includes private equity and venture capital roles in San Francisco, institutional fund investments, direct technology investments for SAP, and angel investing. He also served as junior faculty at Stanford Graduate School of Business, holding degrees from the University of Oxford and Harvard University, and now resides in Utah with his family, passionately solving business challenges.

Connect with Winter on LinkedIn

Learn more about Coolwater

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Everything is degrading in major cities like Toronto.

Violent crime has skyrocketed, homelessness is rampant, living is increasingly unaffordable, and we are paying more in taxes & receiving worse services. In the latest episode of The Profit or Pivot Podcast I am joined by Toronto City Councilman James Pasternak to discuss these myriad issues Toronto is facing.

One story I simply cannot wrap my head around.

A few months ago, a group of ISIS linked terrorists planned kidnappings of Jewish girls for r*pe, torture and ransom. Thank God, their first potential victim was able to escape by yelling for help. Police found weapons such as automatic rifles and plans for various attacks in their homes. And its been credibly reported that at least 1 of them has been released on bail.

Read that again:

A dangerous terrorist caught trying to kidnap girls, who has access to weapons, and a means to carry out attacks has been released. And I bet most of you haven't heard this story.

Its been buried.

Why???

While our discussion is about Toronto, the challenges we face are mirrored in other major cities across the West. James and I unpack some of the underlying causes, and potential solutions.

Watch on YouTube.

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My listeners get 30% off for the 1st three months when you tell them I sent you (or use my link).

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ABOUT JAMES PASTERNAK

James was first elected to Toronto City Council in 2010. He was re-elected in 2014, 2018, and 2022. Prior to coming to City Council he served 4 years as a Trustee on the Toronto District School Board. James is known for advancing creative solutions to complex urban problems and has been a leader in fighting antisemitism and hate in all its forms. James was the founding Trustee of the Africentric Alternative School, was the first to bring the concept of participatory budget making to Toronto, initiated the review of the consequences of drone technology and the implications of e-cigarettes. He was the first on Council to sound the alarm of the consequences  of tariffs and a potential trade war with the United States. James currently serves as Chair of North York Community Council and has Chaired a number of City Council standing committees. He is a lifelong resident of York Centre.

Jim Ferry, a Partner at Volition Capital with $1.7B AUM, recently posted a VC analyst role and received 2,500 applications in one week.

That number alone says everything. In this episode of The Profit or Pivot Podcast, we unpack what that level of competition really means, why traditional career advice is broken, and how hiring managers actually think when they’re flooded with applicants who all look the same on paper.

If you’re trying to get hired into a competitive role, this episode will force you to rethink your approach. This conversation isn’t about polishing résumés or gaming LinkedIn. It’s about thinking like the person doing the hiring.

We get into:

His perspective on investing in the age of AI This episode is a wake-up call for anyone trying to break into competitive roles especially in VC, startups, and high-performance environments. If you want to get hired, promoted, or taken seriously, this conversation will change how you approach your career.

🎧 Listen now and rethink how you stand out.

About Jim Ferry

Jim is a Partner at Volition Capital, a Boston-based Series A / Series B growth equity firm with over $1.7B in assets under management. Volition invests ~$15M to ~$60M in technology startups with a ~$5M+ run rate. Since joining the firm in 2014, Jim has focused on high-growth, founder-owned companies in the internet and consumer sectors. Jim specializes in high-volume transactional businesses across sectors including ad tech, marketplaces, fintech, consolidation platforms, and more, partnering with founders to scale their businesses efficiently.

Connect with Jim

X

LinkedIn

Volition Capital (email)

If you are a high growth startup with a ~$5M+ run rate looking to raise ~$15M-60M, feel free to reach out to Volition Capital:

[email protected]

Who you know in business is critical to your success, especially as a startup. And meeting the right people whether its best employees, partners, customers, and investors often requires networking and meeting new people in person.

But what if you're an introvert like me and dread networking and meeting new people in person?

There are a few simple and easy steps you can implement to overcome your fear, get out of your comfort zone and start meeting new people.

This advice is not limited to business events, but can be implemented more broadly, such as social events. This advice is borne out of my own experience as an introvert after realizing early on that in order to achieve my business and financial goals, I would have to get out of my comfort zone, and meet new people in person at scale. And its worked wonders for me!

Max Abergel signed one of the most influential rappers in the world without an intro, a résumé, or permission. He literally slipped past security and walked into a green room.

That moment led to a long-term partnership with Waka Flocka Flame, an artist with diamond-certified records, collaborations with Nicki Minaj and Drake, and a brand that stretches far beyond music into business, philanthropy, and politics.

But this episode isn’t about celebrity. It’s about the operators behind the scenes, the people who turn influence into a business.

And Max didn’t come from music. He came from tech.

That initial pitch in the green room turned into an 11-year partnership spanning:

Touring and brand deals

Business operations and management

Investments and exits

Building businesses around a personal brand without diluting it

Waka Flocka Flame isn’t just a rapper, he’s a cultural force.

We get into:

The wild story of how Max met Waka and why it worked

How to turn proximity into partnership (without being transactional)

Why brand affinity matters more than follower count

The difference between selling hours vs. building leverage

Lessons from working with one of the biggest artists in the world

Why authenticity compounds over time

What “escaping the matrix” actually looks like in real life

Why most people miss opportunities that are right in front of them

If you’re a founder, creator, or operator trying to build something that lasts, this episode is a real-world lesson in how relationships become platforms.

Every brand is trying to influence you but only a few succeed. Why? Because great brands understand human psychology better than their competitors.

In this episode of the Profit or Pivot Podcast, I sit down with Rena Nickerson, the General Manager of the Quaker and Sabra brands in Canada, who has spent her career understanding how people think, what motivates them, and how to turn that into real business growth.

We go deep into the mechanics of brand building, behavioral influence, and the subtle line between persuasion and manipulation. How do you shape perception? How do you create emotional attachment? Why do some brands scale to millions while others burn out?

Rena also opens up about her own corporate path: learning she was going to be fired, the wake-up moment that forced her to rethink her leadership style, and how that experience reshaped how she approaches communication, team dynamics, and personal identity and being Jewish in the corporate world today.

If you care about marketing, growth, influence, or building something that actually lasts, this episode is for you.

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About Rena Nickerson

Rena is a respected leader within the Consumer Packaged Goods industry. As General Manager, Quaker Canada, she has led a national team of 650 since 2023. Prior to that, she was GM, SodaStream Canada for 7 years, tripling the business.

Prior to joining PepsiCo as a GM, Rena started her career as a marketer on top brands such as Colgate, Campbell and Kraft. You can find her on LinkedIn, where she spends way too much time.

LinkedIn

Ever wondered how the Russian oligarchs were made? This episode gives you a glimpse into that world… through someone who lived it, built through it, and survived it.

In this episode of The Profit or Pivot Podcast, Matan speaks with Marat Ressin, an entrepreneur who built and bought over 30 businesses after the fall of the Soviet Union, escaped the rising control of the KGB to Canada, and went on to build the #1 ranked university-linked business accelerator in the world.

Marat shares his unbelievable journey:

This is one of the most insightful, candid, and inspiring founder stories you’ll hear.

About Marat Ressin

Marat is the founder of the York Entrepreneurship Development Institute (YEDI), a globally top-ranked university-linked accelerator, professor, turnaround specialist, real estate developer, and serial entrepreneur with 30+ business acquisitions across multiple industries.

Learn more about YEDI

Connect with Marat

By his mid 20's, Ryan Henry became Head of Engineering for a fast growing mobile game developer. It was his first exposure to scaling a tech company, which he later leveraged at Freshbooks, a Canadian "unicorn" startup (over $1 billion valuation). At Freshbooks, Ryan hired 100 engineers in 1 year, a real rocket ship. He shares his insights on scaling a business, hiring the best people, how AI will change the tech landscape, and other important learnings.

Ryan also launched a startup and now runs a VC fund, Sand Hill North, where he invests in Seed stage companies in Canada and the US.

In this conversation, we focus a lot on what is considered a venture scalable business, how VCs think through an investment, and why entrepreneurs need to adopt a VC scalable perspective if they choose to raise money.

Entrepreneurs and investors will gain a lot from hearing Ryan's perspective.

Don't miss out!

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About Ryan Henry

Ryan manages venture investments at Sand Hill North, focusing on pre-seed and seed B2B software in Canada and the US. They invest in day-0 companies with a particular focus on robotics, energy and AI. Previously, Ryan co-founded Wisely, an AI-powered fundraising enablement platform for charities, and scaled FreshBooks from their series-A.

With over a decade of leadership experience, Ryan has built SaaS, AI, fintech, mobile games and AR apps and worked with brands like Disney, Mattel, and McDonald's.

Connect with Ryan

Website 

LinkedIn 

X: @IAmRyanHenry

Geoff became an accidental entrepreneur building a 150 employee business and becoming a prolific angel investor with investments that include a $500 MILLION exit.

Geoff's journey illustrates the unpredictable path of entrepreneurship, highlighting the importance of adaptability, continuous learning, and being open to unexpected opportunities. Geoff and I discuss how to build a business, the many tough choices one has to make, and the big mistakes entrepreneurs make in their journey.

We also discuss how to more effectively raise venture capital, pitfalls to avoid, and whether or not VCs rely on luck or skill to succeed themselves. If you're an aspiring VC investor or entrepreneur, you don't want to miss out on Geoff's insights! 

Connect with Geoff:

LinkedIn 

Looking for an accelerator:  altitudeaccelerator.ca