Change Order Podcast

Markets can stay irrational longer than you can remain solvent.

If you’re a VC, you’ve likely lived through this.

Both public and private markets change in a flash, but human nature stays the same.

Amidst this, an anti-VC investor emerges.

Meet James O’Shaughnessy, Founder and CEO of O'Shaughnessy Ventures LLC.

Previously, James founded and chaired OSAM, an asset management firm, and served as Director of Systematic Equity at Bear Stearns Asset Management.

In this conversation with Primary GP, Jason Shuman, James dives deep into avoiding biases as an investor, why he has no LPs, and how it pays to be lazy as a VC.

ABOUT US:

Primary is the largest early-stage venture firm in the world, with over $1B in Assets Under Management, and notable investments under its belt include unicorns like Slice, Chief, Electric, and more.

With a dedicated team of Partners, Associates, and Advisors, Primary operates with one clear modus operandi: to allocate unreasonable resources toward building unfair advantages.

Follow us on LinkedIn:

• James O’Shaughnessy
• Jason Shuman

• Primary Venture Partners

00:00:00 Trailer

00:01:02 Introduction

00:06:33 How history repeats itself with every innovation

00:09:34 The role of premeditation in achieving success

00:18:25 Differing views on premeditation in investing

00:20:23 What sparked James's passion for the stock market

00:25:21 The story behind O’Shaughnessy Capital Management

00:32:32 Thinking Like a Quant in Venture Capital

00:38:13 The evolution of market structures in AI technology

00:46:25 Why private companies win

00:53:13 Using AI to enhance critical thinking

00:59:22 The secret to becoming a top Venture Capitalist

01:05:40 How to avoid 50% of failures in Venture Capital

01:10:27 How the Internet revolutionized philanthropy

01:14:46 Why parents should encourage kids to Google

01:17:19 The one change James would make as Mayor of New York

44 million American households pay rent every month.

What incentive do they have, apart from the obvious deterrent of being homeless?

Zilch. Nada.

Our guest, Ankur Jain, and his team are switching things up.

Born to immigrant parents, he sold his company to Tinder, and became VP of Product.

Today, he spearheads Bilt Rewards and Kairos.

Ankur shares how missing the cut for his basketball team became his first business deal, his mission to reward renters with ownership, and partnering with Wells Fargo and Mastercard to further this mission.

ABOUT US:

Primary is the largest early-stage venture firm in the world, with over $1B in Assets Under Management, and notable investments under its belt include unicorns like Slice, Chief, Electric, and more.

With a dedicated team of Partners, Associates, and Advisors, Primary operates with one clear modus operandi: to allocate unreasonable resources toward building unfair advantages.

Follow us on LinkedIn:

• Ankur Jain
• Jason Shuman
• Primary Venture Partners

00:00 Trailer

00:55 Introduction

06:18 The Life-Changing Impact of Early Career Exposure

08:17 Turning a Rejection Into a First Business Win

11:54 Spending Discipline is Key for Startup Growth

15:07 The Cold Start Problem in Launching Loyalty Program

19:33 How a Unique Loyalty Program Secured Major Bank Deals

25:42 The Strategy Behind Winning Big Deals in Tech

34:39 Unlocking Startup Agility with the Pod Model

41:21 Creating a Culture of Possibility

43:16 How to Identify Culture Fit During Hiring

44:17 How History Influences Modern Business Tactics

54:03 Winning Strategies from Alibaba's Playbook

01:02:01 Lessons from Startup Incubation in College

Are there too many baby boomer businesses up for grabs? Codie Sanchez thinks so.

With 60% of U.S. small businesses owned by baby boomers, she believes the real risk is that no one steps up to buy them.

For Codie, what began as a quiet side hustle at Goldman Sachs has grown into an extensive portfolio of small businesses—the kind private equity ignores but, as she insists, you should capitalize on.

In this episode of Change Order with Jason Shuman, she explains why:

• baby boomer businesses are ripe for acquisition,

• you don’t need an MBA for M&A, and

• it’s essential to “know yourself” and self-reflect.

Codie also discusses her new book, "Main Street Millionaire: How to Make Extraordinary Wealth Buying Ordinary Businesses," sharing insights from her time on Wall Street on strategic acquisitions and the importance of self-awareness in building long-term wealth.

ABOUT US:

Primary is the largest early-stage venture firm in the world, with over $1B in Assets Under Management, and notable investments under its belt include unicorns like Slice, Chief, Electric, and more.

With a dedicated team of Partners, Associates, and Advisors, Primary operates with one clear modus operandi: to allocate unreasonable resources toward building unfair advantages.

Follow us on LinkedIn:

• Codie Sanchez
• Jason Shuman
• Primary Venture Partners

(00:00) Trailer

(01:07) Welcome to Change Order

(02:31) The Decline of Business Ownership

(04:08) The Silver Tsunami and Wealth Transfer

(04:57) The Rise of Small Business Acquisitions

(07:31) Challenges and Opportunities in Business Ownership

(09:36) The Role of Private Equity and Finance

(30:47) The Future of Business Education

(42:41) Ownership Dynamics in Venture Capital

(43:24) Commitment and Board Seats

(44:07) Evaluating Founders and Operators

(46:19) Interview Techniques and Job Fit

(47:56) Work-Life Balance in Startups

(49:37) Geographic Considerations in Business Deals

(52:22) The Reality of Business Ownership

(54:52) Finding and Acquiring Businesses

(01:05:39) Time Management and Leadership

(01:12:12) Risk and Self-Doubt in Entrepreneurship

(01:17:12) Regulation and Common Sense Governance