The AI Why with Liam Lawson

In this episode, Braden Warwick, Financial Planning Product Architect at PWL Capital, breaks down why so much of the financial advice sold at big banks is a sales pitch dressed up as a plan, and what a real financial plan actually requires. Braden traded a PhD in aerospace engineering for a career rebuilding how Canadians plan their money, and he brings that same engineering mindset to financial planning: define your objectives, map your constraints, then solve for the outcome that actually improves your life.

Braden also walks Liam through the AI infrastructure PWL has built in house, from a proprietary data lake to an AI powered meeting note tool and planning summaries, and explains why they chose to build their own tools instead of buying off the shelf software. They get into Monte Carlo simulations, why financial planning is really about the distribution of outcomes rather than one predicted path, and what a financial planning engagement might look like in 2031.

Key Topics Covered

How Braden went from a PhD in aerospace acoustics to building financial planning tools at PWL Capital

Why PWL's advisors are paid for advice, not for selling products, and how that changes the plan you get

The six areas of a real financial plan: investing, cash flow, tax, insurance, retirement, and estate

Treating a financial plan like an engineering problem: objectives, variables, and constraints

Why Monte Carlo simulations model financial planning as a distribution of outcomes, not one fixed path

What forms of uncertainty most financial software still misses, from real estate values to life expectancy

Why PWL built its own AI meeting note tool and data lake instead of buying an off the shelf solution

How AI is helping PWL's advisors scale personalized, evidence based financial plans

PWL's acquisition by One Digital and what it changed, and did not change, about how Braden works

What a financial planning engagement could look like by 2031

Episode Timestamps

00:00 - Introduction

00:40 - From aerospace engineering to financial planning

03:54 - Why PWL approaches financial advice differently

07:31 - The six areas of a real financial plan

11:48 - Financial planning as an engineering problem

17:56 - The psychology behind financial planning

23:14 - Objectives, constraints, and uncertainty

28:10 - How Monte Carlo simulations work

33:21 - What financial planning software still misses

39:11 - Building financial planning tools at PWL

44:16 - Inside PWL's financial planning system

51:38 - How AI is changing the advisor workflow

57:20 - Why PWL built its own AI tools and data infrastructure

1:03:41 - What changed after the OneDigital acquisition

1:06:34 - The future of financial planning

1:11:47 - Why Braden does what he does

Braden's Socials:
LinkedIn - https://www.linkedin.com/in/braden-warwick-a40b48a3/

Resources Mentioned:

Braden’s article, The Optimal Financial Plan - https://pwlcapital.com/the-optimal-financial-plan/

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In this episode, Andrew McNamara, VP of Applied ML at Shopify, returns to unpack how much has changed in agentic commerce since his last episode. Andrew and Liam dig into why agents are becoming "the new front door to commerce," why orders coming to Shopify stores from AI are up 13x, and what's actually happening inside Shopify's personalized shopping agent in the Shop app.

They also get into the Universal Commerce Protocol (UCP) and why AI commerce is growing 9x faster than social commerce did at the same stage, how Sidekick's architecture and app extensions work, and SimGym, Shopify's system for training AI shoppers to A/B test store changes before they ever reach a real customer.

Key Topics Covered

How shopping is shifting from stores and desktops toward agents as "the new front door to commerce"

Why orders coming to Shopify stores from AI are up 13x, and why catalog-powered AI search converts twice as well as general AI search

Inside Shop app's personalized shopping agent, and how it learns different shopping personas (like shopping for a pet versus a child)

Why customers are shifting from keyword searches to natural language queries, and the higher conversion rates that come with it

Why Shopify keeps shopping data personalized to the individual user rather than training it into a larger internal model

What the Universal Commerce Protocol (UCP) is, and why AI commerce is growing 9x faster than social commerce and 3x faster than mobile did at the same stage

The story of Shopify's CEO giving his own Hermes agent a budget so it can send him gifts in the mail

Sidekick's app extensions, and how partners like Klaviyo and Loop plugged in at launch

Campaign Autopilot's "auto research loop," and its parallels to reinforcement learning

SimGym, and how Shopify trains AI shoppers to A/B test store changes before running them on real customers

Why Sidekick runs on Anthropic's Sonnet model hosted on Google Cloud, and why that choice is model agnostic

Andrew's own habit of shopping by taking pictures throughout the week and searching by image through UCP-connected agents

Episode Timestamps:

00:00 - Introduction and welcome

00:29 - What's changed in AI and shopping since their last conversation

01:47 - Agents becoming "the new front door to commerce"

04:16 - Inside Shop app's personalized shopping agent

07:32 - Why data stays personalized to each shopper instead of training a larger model

11:53 - What the Universal Commerce Protocol (UCP) is, and orders from AI up 13x

14:58 - Merchant tooling for tracking AI-driven traffic and conversions

15:55 - The story of Tobi's Hermes agent sending him gifts in the mail

20:48 - Andrew's own habit of shopping by taking pictures and searching by image

26:59 - Sidekick's app extensions and partner integrations

33:02 - Inside Sidekick's architecture: the Sonnet model and knowledge base

35:18 - Campaign Autopilot's auto research loop

38:58 - SimGym: training AI shoppers to test store changes

42:23 - What's next for Shopify's agentic commerce features

44:17 - Where to find Andrew

Andrew's Socials:

Twitter (X) - https://x.com/DrewCH

LinkedIn: https://www.linkedin.com/in/andrewmcnamara1/

Partner Links

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David McIntosh, Chief Connected Stores Officer at Instacart, joins Liam to explain why the company is betting on smart shopping carts instead of rewiring stores with ceiling cameras. David walks through the $350 million acquisition of Caper, how Instacart is now live in more than 100 cities with thousands of connected carts, and why the screen on the cart, not the checkout speed, turned out to be the real driver of sales lift for retailers.

David also gets into the surprisingly hard engineering problems behind a smart cart, like figuring out whether a basket is actually empty, fusing camera and scale data in real time, and building recommendations that know exactly where a shopper is standing in the store. He and Liam talk about who owns all that shopping data, what agentic AI looks like when it moves from chat into the aisle with tools like Cart Assistant, and why grocery budgets and meal planning are becoming one of the most requested AI features in the store.

Key Topics Covered

Why David left Tenor, the GIF search engine used by billions, to build Instacart's Connected Store business

The strategic bet behind unifying online and in-store grocery shopping

Why Instacart acquired Caper for $350 million instead of building smart carts in-house

The reason Instacart chose carts over ceiling cameras for in-store AI

How a simple running total and real-time coupons drive measurable sales lift

The NVIDIA Jetson hardware and multimodal sensor fusion that let the cart "see" what's in the basket

The strange edge cases in physical AI, like why "is this cart empty" is a genuinely hard question

Who owns retailer and shopper data, and how it's used to improve recommendations

Cart Assistant: how Instacart lets customers shop inside ChatGPT and directly on retailer websites

Using agentic AI to fix store operations like out-of-stock items and supplier issues

How budget-conscious meal planning became one of the most requested AI features in the store

David's answer to Liam's closing question: why he does what he does

Episode Timestamps
00:00 - Introduction and welcome
00:14 - David's path from Tenor to Instacart's Connected Store
02:01 - The bigger bet behind bringing online and in-store shopping together
05:29 - Entering the smart cart market and acquiring Caper
08:07 - Caper's scale today: 100+ cities and millions of daily sensor inputs
10:28 - How the smart cart actually drives sales lift
12:49 - Why Instacart bet on carts instead of ceiling cameras
17:33 - The unglamorous detail that makes or breaks adoption: charging
19:26 - What makes the experience sticky enough to keep customers coming back
24:41 - Inside the hardware: NVIDIA Jetson and multimodal sensor fusion
28:43 - The strange edge case behind a seemingly simple question
35:14 - Who owns the shopping data, and how retailers use it
37:30 - Agentic shopping: Cart Assistant and buying inside ChatGPT
42:16 - Using agentic AI to fix store operations, not just shopping
46:17 - Why David does what he does

Connect with David on LinkedIn:
LinkedIn: https://www.linkedin.com/in/mcintoshdavid/

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In this episode, Zachary Smith, CEO and co-founder of Datum and previously the founder of Packet (acquired by Equinix for $335M) and Voxel (acquired for $35M), joins Liam to explain why the internet is about to undergo its biggest transformation since the cloud. As AI agents, vibe coding, and thousands of new applications flood the web, Zac believes the open internet model we've relied on for decades is breaking down.

Zac argues that every person, every company, and eventually every AI agent will need its own private network. He explains why the future internet may look more like the Visa network than today's public web, how digital sovereignty and geopolitics are reshaping infrastructure, and why developers are increasingly relying on dozens of cloud services rather than just the hyperscalers.

The conversation also dives into Zac's unlikely journey from Juilliard-trained musician to building and exiting two infrastructure companies, the emotional toll of entrepreneurship, and why he keeps coming back to startups despite already having financial freedom.

Key Topics Covered

Zach's journey from Juilliard and classical music to building infrastructure companies

Building Voxel and selling the company for $35M

Starting Packet and its $335M acquisition by Equinix

Why AI agents are creating a security problem for the internet

Why every person and company may eventually need a private network

The difference between the public internet and private internet

Why the future internet could resemble the Visa network

Digital sovereignty, geopolitics, and the splintering of the internet

Why developers increasingly rely on dozens of cloud providers

How AI is turning millions of people into software developers

APIs, MCP, and the next phase of application architecture

Why Zach believes AI agents should only talk to approved systems

Open source, network effects, and Datum's long-term vision

The emotional side of entrepreneurship and why community matters more than money

Episode Timestamps
00:00 Introduction and welcome
00:06 Zach's background: from Juilliard and classical bass to startups
02:44 Building Voxel and the early cloud era
08:44 Starting Packet, raising capital, and the Equinix acquisition
15:28 Why taking time off helped him dream again
18:02 What Datum does and the idea of a network cloud
19:38 Three forces changing the internet
20:41 Hyperscalers explained: Amazon, Google, and Microsoft
24:52 Why new cloud providers are emerging
27:16 Digital sovereignty and the fragmentation of the internet
32:03 Public internet vs. private internet
32:54 Inside the physical "meet me rooms" that connect the internet
39:49 How internet routing actually works
45:56 Why developers use so many cloud providers
48:10 APIs, MCP, and AI agents
51:07 Why the future internet may resemble the Visa network
54:23 Who Datum's customers are, and why Datum is open source
1:03:07 AI agents and the next generation of software
1:07:50 Why Zach keeps building companies, and why he does what he does

Connect with Zac:
LinkedIn: https://www.linkedin.com/in/zsmith/
Website: https://www.datum.net/

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Vinay Gidwaney is Chief Product Officer and Mike Sullivan is Co-Founder and Chief Growth Officer of OneDigital, a 6,000-person, PE-backed benefits, HR, and wealth consultancy serving roughly 100,000 employers. Their contrarian bet: AI transformation has almost nothing to do with technology and everything to do with treating AI as talent. Instead of automating tasks, OneDigital built an internal hiring pipeline for AI, complete with job descriptions, an intern-to-apprentice-to-full-time promotion path, and performance improvement plans, and used it to avoid the layoffs most "AI transformation" playbooks assume are inevitable.

Liam sits down with both of them to unpack the night Mike built a "disruption calculator" that showed OneDigital was on track to cut 1,800 of its 6,000 jobs, and how that all-nighter became the catalyst for a different strategy. They get into Ben, the AI coworker now handling daily conversations with 1,600 benefit consultants, why Vinay cites a claim from Lemonade's CEO that AI agents scored higher on customer empathy than human call center staff, the risk of companies "renting back" their own intelligence after gutting their workforce, and the thinking behind their upcoming book, Workforce Intelligence, releasing August 25th.

Key Topics Covered

Why treating AI adoption like rolling out a new CRM guarantees failure

The failed early bet on automating RFPs, and why augmenting human thinking won instead

The stat that proves AI adoption is personal: a manager's own AI use doubles their team's usage

Building an AI "disruption calculator" overnight, and the 1,800-job number it produced

OneDigital's three-part AI framework: coworkers, builders, and agents

How OneDigital literally hires its AI: job descriptions, interns, apprenticeships, and performance improvement plans

Meet Ben, the AI coworker fielding daily conversations with 1,600 benefits consultants

Why they stay LLM-agnostic and separate the intelligence layer from the model and the harness

The real risk behind AI cost metering: losing access to the intelligence your company now depends on

A claim from Lemonade's CEO that AI agents beat humans on customer empathy

Irreducible vs. reducible skills: how to decide what AI should do and what humans should keep

The case for "faces, not headcount" and OneDigital's internal "humanity test"

What's actually inside their upcoming book, Workforce Intelligence

Episode Timestamps
00:00 Introduction
00:41 The thesis: AI transformation is about talent and leadership, not technology
02:44 Why treating AI adoption like a CRM rollout fails
04:29 Pitching VCs a "Workday for AI agents," and why it flopped
07:19 Why automating tasks failed, and augmenting human thinking won
11:20 The stat that changed everything: manager AI usage doubles team usage
15:04 Mike's personal epiphany and the "Claude" nickname from his family
18:10 Building an overnight "disruption calculator" with Claude and Replit
19:56 The result: a model showing 1,800 of 6,000 jobs at risk if nothing changes
21:11 Coworkers, builders, and agents: OneDigital's three-part AI framework
24:02 The AI hiring pipeline: job descriptions, interns, and apprenticeships
27:39 Meet Ben: the AI coworker now used by 1,600 benefits consultants daily
31:10 What's actually deployed: an LLM-agnostic stack with a separate intelligence layer
35:38 The metering and access risk: the Fable/White House security scare
39:56 Measuring "workforce intelligence": blending human and AI capability
50:07 Irreducible vs. reducible skills, and the Lemonade insurance AI-empathy example
53:38 The reskilling problem, and why human judgment stays irreplaceable
56:30 "Faces vs. headcount" and the company's internal "humanity test"
1:07:08 The origin of their book, Workforce Intelligence (out August 25th)
1:11:10 The risk of "renting back" your own intelligence after cutting your best people

Learn more about OneDigital and the book Workforce Intelligence: https://www.onedigital.com/

Connect with Mike on LinkedIn: https://www.linkedin.com/in/mikesullivanatdigital/
Connect with Vinay on LinkedIn: https://www.linkedin.com/in/gidwaney/

Partner Links
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