What if gaining success only raises the stakes?

Having operated at the center of scale, Michael Tannenbaum, the former COO of Brex and now CEO of Figure and Arthur Levy, CBO of Brex, share how they’ve kept their edge, and where AI is pushing fintech next.

They join Jason Shuman to discuss:

• ​there’s more to operating than being great at finance
• ​how saying ‘no’ becomes the hardest part of success
• ​why financial services should focus on Blockchain over AI
• ​why AI is still being used as an experimental tool by enterprises

Connect with us here:

1. ​ Michael Tannenbaum- https://www.linkedin.com/in/michaeltannenbaum/
2. ​ Arthur Levy- https://www.linkedin.com/in/arthurlevy/
3. ​ Jason Shuman- https://www.linkedin.com/in/jasonshuman/
4. ​ Change Order- https://www.linkedin.com/company/change-order/
5. ​ Primary Venture Partners- https://www.linkedin.com/company/primary-venture-partners/

00:52 Introduction & Guest Background

01:11 VC-to-Operator Transition

01:50 Choosing SoFi: Strategy & Early Growth

03:07 SoFi’s Scale & Role Scope

05:52 First Meeting in Cancun & Boston Roots

07:02 Reconnecting in San Francisco & Partnerships

09:14 Mentor-to-Peer Dynamics

11:06 Recruiting Art to Brex & First Republic Deal

15:45 Role Evolution & Career Pivot at Brex

20:26 Fall ’23 Crisis & Strategic Refocus

22:04 “Big Rocks” Focus Framework

24:34 AI vs. Blockchain in Financial Services

29:59 Internal AI Adoption & Use Cases

33:02 Reimagining Sales Motion with AI

38:35 Market Segmentation & Customer Focus

41:43 Rapid-Fire Insights: Mistakes, Books, Mayoral Picks

49:24 Blockchain & Stablecoin in Capital Markets

53:02 Leading AI Adoption: Teams & Strategy

56:46 Future of SDR & GTM Roles with AI

59:59 AI’s Broader Impact on Ecosystem

1:04:27 Rapid-Fire Round: Personal Picks

1:09:51 Closing Remarks & Outro

Is AI a threat to creativity or the ultimate creative assistant?

Shane Hegde, Co-founder and CEO of Air, believes it’s the latter. 

With roots in creative writing and a career pivot into computer science, Shane set out to build a platform that leverages AI to free creative teams from routine tasks.

In this of episode of Change Order⁠, he joins Jason Shuman⁠ to unpack:

• why every brand needs creativity as an expression of its identity
• why it is a waste of time for companies to try to be the best at everything
• how constantly seeking mentors helps you level up
• why he admires Shopify’s approach
• how Air plans to evolve into the platform that takes you from 1 to 100

Connect with us here:

1. Shane Hegde
2. Jason Shuman
3. Change Order
4. Primary Venture Partners

00:00:00 Trailer

00:00:46 Introduction

00:01:01 Ruined by AI?

00:06:35 Next gen mass market creative

00:12:16 Approaching creative work

00:17:09 Evolution and demand

00:31:04 100x easier

00:36:51 Closed vs open ecosystem

00:45:40 Constraints breeds creativity

00:53:56 Pushing the envelope more

00:59:01 Playing at the bottom

01:01:43 Growing up as a founder

01:07:55 What would you change?

01:13:31 Outro

Solving Hollywood’s pain with vertical fintech.

Ali Javid, CEO and Co-founder of Wrapbook, and his team want to make sure no one gets left waiting.

In this episode of Change Order he joins Jason Shuman to reveal how Wrapbook helps production teams handle payroll and accounting more smoothly and quickly.

On the docket:

• how Wrapbook digitized payroll from end to end 

• why trade wars must factor in America’s soft power in film 

• why founders can't think like VCs 

• how merit is the gate and then DEIB very much matters

Connect with us here:

1. Ali Javid- https://www.linkedin.com/in/alijavid/

2. Jason Shuman- https://www.linkedin.com/in/jasonshuman/

3. Change Order- https://www.linkedin.com/company/change-order/

4. Primary Venture Partners- https://www.linkedin.com/company/primary-venture-partners/

00:00 Introduction

00:17 Trailer

01:20 Strengths and weaknesses

07:56 Global problems in Hollywood

11:36 Chasing paper

15:29 Hard tech and an exit

18:36 Confidence in conviction

22:53 Trust, payroll, character

31:56 Challenging wartime moments

34:40 MrBeast, Apple TV+, AI

42:25 Change, thanks to AI?

48:32 Scaling and culture

50:47 Rhetoric has changed

53:44 Every person is created equally

57:33 What would you change?

59:51 Outro

In S1, Jason Shuman spoke with Ryan Serhant, Codie Sanchez, and Ankur Jain about steering through change.

Season 2 brings Ali Javid, Michael Tennenbaum, Shane Hegde, and more into the conversation, exploring the crucibles that have shaped their journeys.

Links to the new YouTube, Spotify, and Apple Podcasts feeds are in the comments.

In a market where Manhattan offices sit empty and $1.5T in real estate debt awaits refinancing, timing is paramount. Ask Scott Rechler—he sold his company at the peak in '07, waited out the crash, then built RXR into a $17 B GAV empire.

In this episode of Change Order, hosted by Jason Shuman, he shares:

• how he built a $6B business— twice

• handling Carl Icahn's hostile takeover bid

• what he learnt from Sam Zell & Danny Meyer

• how he trusted his gut over family and shareholder advice

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:

• Scott Rechler

• Jason Shuman
• Primary Venture Partners

(00:00:00) Trailer

(00:00:45) Introduction

(00:01:00) Founder Drift

(00:03:00) Focus

(00:06:50) The template and the process

(00:09:16) Investors and firm builders

(00:12:09) Entrepreneurial mindset

(00:15:31) Understanding business intricacies

(00:19:58) Engagement strategy

(00:23:10) IPO insights and decisions

(00:30:28) Public vs Private

(00:33:27) Highly efficient private market

(00:36:12) The January 7 acquisition

(00:40:57) Secession planning

(00:43:25) Starting RXR a day later

(00:45:27) Self-funding 150 employees

(00:47:03) A blank piece of paper

(00:48:51) Recession

(00:53:56) Sam's story

(00:57:02) Maintaining conviction

(00:59:18) Expanding beyond familiar markets

(01:05:41) New York

(01:07:56) RXR Involvement and startup insights

(01:12:33) Qualities of startup founders

(01:16:29) Mayor of New York

(01:17:45) Outro

Meet Ryan Serhant, the CEO of SERHANT, and star of the hit show, "Million Dollar Listing New York” we all love.

From struggling actor to real estate mogul, Ryan’s journey is nothing short of inspiring.

In this episode, he shares:

• How he grew from $9,200 to $2B in sales in 2022, with sights set on $5B in 2024

• The applications of AI in real estate

• How being an actor taught him sales

• The ups and downs of using his TV fame to build trust in a tough market

Ryan’s story is about more than sales or even real estate—it’s about adapting, innovating, and connecting.

• Ryan Serhant
• Jason Shuman
• Primary Venture Partners

In this episode of Change Order, Jason Shuman (General Partner at Primary) sits down with Arthur Levy (Chief Business Officer at Brex) to hear his extraordinary journey, from his venture capital roots to becoming an indispensable operator at Brex.

Arthur shares the pivotal decisions that shaped his path, reveals how to form strategic partnerships, and unpacks the significance of grit and personal connections in the business world.

Learn Arthur’s playbook for networking with authenticity and how he made the successful transition from investor to operator.

Connect with Primary: https://primary.vc/people

00:00 Introduction

01:29 How Arthur made the jump from investing to operating as Brex's CBO

06:56 How Arthur pitched to Brex his perfect role

09:56 Betting your career on a startup's founders

11:28 Brex's positioning and market change

13:15 What defines the best founders

16:08 Advice for young investors considering a career as a VC

18:30 Balancing being blunt and being effective as an operator

22:03 Dealing with rejection with business partnerships

24:18 How Arthur and Brex thinks about competition

25:33 The challenges Brex faced to validate their first product

27:44 The power of networking in the right circles

28:55 What is a Chief Business Officer?

29:56 Lessons from Arthur's role at Brex for evaluating the best talent

32:24 Why Art prioritises in-person meetings and showing up

34:13 What Arthur's father taught him

36:16 Where Arthur got his business acumen

37:02 The winning culture at high-performing companies

38:39 How to assess the drive of founders

39:40 Being open to cold outreach messages because "no's are free”

42:18 Tactical advice to make intros as easy as possible

• ⁠Arthur Levy⁠

• ⁠Jason Shuman⁠

• Primary Venture Partners

Ilir Sela, Founder & CEO of Slice, grew up with pizza in his DNA—his family ran pizzerias in NYC, so he knew the grind inside out.

Watching mom-and-pop pizza shops get left behind, he bootstrapped MyPizza in 2009.

What started with Ilir entering orders in a Starbucks has grown into Slice—a platform now driving $1B+ in GMV for 20,000+ independent pizzerias, saving them $265M.

Primary is proud to have backed Slice from the seed stage.

In this conversation, Jason Shuman and Ilir get into:

• how Slice evolved from mypizza.com

• the power of bootstrapping early

• how North Macedonia became a talent hub for Slice

• why even 1% M-O-M churn can cripple your startup

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:

• Ilir Sela

• Jason Shuman

• Primary Venture Partners

(00:00) Trailer

(01:33) The Rise of Slice and Its Macedonian Roots

(06:08) Family Legacy in the Pizza Business

(14:22) The Birth of Nerdforce

(22:12) The Evolution of MyPizza to Slice

(30:21) Vertical vs Horizontal Platforms

(33:49) Building a Strong Sales Culture

(39:43) The Role of AI in SMB Tech

(45:42) Venturing into Supplies and VC Funding

Not every experienced leader thrives in a startup. Few people understand this better than Kat Cole.

As President & COO of AG1, she’s leading its growth in 60+ countries, driving a global health initiative poised to transform the $6.3 trillion industry.

In conversation with Jason Shuman, Kat unpacks:

- why 90% of pitches are dead on arrival,

- subtle cues that expose a weak founder within minutes and,

- the delicate balance between inspiring teams and over-convincing stakeholders

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:

• Kat Cole

• Jason Shuman
• Primary Venture Partners

00:00 Trailer

01:02 Introduction

01:08 Becoming unpopular, going to the unfamiliar

07:36 A learning machine

09:49 Building teams

11:39 Selecting executive talent

14:02 Recruiting and listening

18:31 Deep and annoying questions

21:37 Red flags

23:31 Trying to sell work

25:11 Leading in crisis

32:22 Over communicating at work

37:48 Skip level meetings

41:48 Positive intent

44:33 The compliment sandwich disproven

46:41 Climbing the learning curve as an executive

53:30 Almost very little matters without health

58:56 Frameworks around big life changes

1:02:16 AI's impact in the e-commerce world

1:04:53 If you were the mayor of New York

1:06:08 Outro

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