Anthony Chiaravallo is the Founder and CEO of Vallo Media, a performance marketing agency that’s helped brands from startups to Fortune 500s—including Nike, Amazon, and FedEx—turn ad spend into measurable growth. With 16+ years of experience and more than $100M in media spend managed, Anthony is a recognized thought leader and PR Week 40 Under 40 honoree, known for cutting through vanity metrics to focus on real business outcomes.

With deep expertise in paid media, performance strategy, and scaling growth engines, he offers insights into how startups and established companies alike can avoid costly mistakes, build full-funnel systems, and leverage AI to stay competitive in today’s fast-changing landscape.

In this episode, he discusses the philosophy behind performance marketing, the myths that frustrate him most, and the future of paid media in the age of AI.

In Today’s Episode We Discuss:

00:00 – Anthony’s background: from sales to launching Vallo Media

01:24 – Breaking into digital marketing and moving from sales to strategy

03:20 – From big agencies to starting his own firm during COVID

05:30 – The freedom and growth potential of entrepreneurship

06:43 – Defining performance marketing and why it still matters today

07:52 – The biggest mistakes startups make with paid ads

10:31 – When startups should turn on performance marketing

12:39 – Why outsourcing to experts often saves time and money

14:20 – Case study: scaling Pliables from a sidewalk stand to a $100M+ acquisition

20:58 – Why clicks and impressions don’t equal results

22:29 – KPIs that actually matter for growth

25:59 – How to know when to scale or move on from a channel

28:03 – Best starter channels and the rise of AI-driven discovery

30:48 – How AI is reshaping paid media campaigns

34:07 – The future of search with ChatGPT, Gemini, and AI assistants

37:15 – The importance of creative in performance marketing

41:46 – Why you should start at the top of the funnel

43:40 – Balancing the art and science of marketing

45:45 – The most frustrating performance marketing myth

47:11 – The most misunderstood part of campaign attribution

49:48 – The future of paid media in the next 3–5 years

52:36 – Rapid fire wrap-up: metrics to kill, favorite brands, overrated platforms, and more

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Dr. Matthew Jones is a licensed psychologist turned startup co-founder coach and cofounder of Co-Founder Clarity. With six years of experience working with hundreds of entrepreneurs—from YC to Sequoia-backed teams—he specializes in helping founders prevent burnout, resolve conflict, and build stronger, more resilient partnerships. His work has been featured in TIME, Business Insider, and Inc., and his new book The Co-Founder Effect dives into the psychology of what makes or breaks founding teams. In this episode, he unpacks the hidden dynamics that shape co-founder relationships and offers practical tools founders can use to scale both their companies and their partnerships.

In Today’s Episode We Discuss:

00:01 – Introduction: Dr. Matthew Jones’ background as a psychologist turned co-founder coach

01:00 – From clinical psychology to startups: helping friends navigate co-founder conflict

02:15 – Couples therapy lessons applied to co-founder relationships

05:15 – The “Co-Founder Effect”: why co-founder dynamics make or break startups

07:20 – Overlooked dysfunctions during company formation and founding with friends

10:40 – Defining co-founder conflict: the three languages all teams speak

13:00 – Why surface-level disagreements often mask deeper relational issues

15:40 – Equity splits, unequal contributions, and renegotiating fairness over time

18:20 – Attachment styles and how they shape co-founder interactions

22:30 – Are startups or marriages more “saveable” with equal dysfunction?

25:40 – Recognizing burnout in founders and its impact on relationships

29:00 – Sustainable work-life balance and recalibrating founder energy

32:20 – Why what got you from 0→1 will break you at 1→100

34:30 – Turning conflict into progress: containers, reflective dialogue, and frameworks

38:40 – Preventing messy breakups: co-founder syncs and co-founder dates

40:30 – Traits of great co-founder duos vs. subtle signs of trouble

42:00 – What VCs often miss when evaluating co-founder dynamics

46:00 – Under-researched realities of co-founder breakups and the need for better data

47:30 – Surprises and lessons learned while writing The Co-Founder Effect

50:53 – Sequencing, editing, and advice for first-time authors

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Damir Ibrahimagić Kopinić is a seasoned early-stage investor, advisor, and private asset manager who has spent decades at the intersection of high finance and early-stage tech. As co-founder and CEO of G Plus Quant, he helps bridge top startups with global venture capital, LPs, and family offices. With experience spanning asset management, trading, blockchain, and beyond, Damir offers a unique perspective on how capital markets and emerging technologies shape the future of venture.

In this episode, he shares his journey from traditional asset management to early-stage investing, the rise of AI-powered startups, and the evolving dynamics between founders, VCs, family offices, and LPs. Damir also unpacks how AI is transforming due diligence, deal flow, and even the structure of venture funds themselves.

In Today’s Episode We Discuss:

00:01 – From asset management to early-stage venture: Damir’s journey

02:20 – ICOs, blockchain, and lessons from the early crypto wave

03:06 – The #1 mistake founders make when pitching investors

05:14 – Why AI dominates investor attention in 2025

07:17 – How AI is making startups leaner and more capital efficient

08:04 – The overlooked value in non-AI deals

09:56 – The risk of AI startups becoming obsolete overnight

11:19 – Vertical vs. sub-vertical AI opportunities (e.g., legal tech)

11:59 – Startups scaling to $100M ARR with tiny teams

13:19 – Family offices vs. institutional LPs: how they differ

15:54 – Why warm intros matter and cold outreach fails

17:33 – Niche vs. generalist funds: which strategy works for emerging managers

22:22 – How LPs evaluate fund decks, deal flow, and GP presentation

24:41 – Why raising a $30–50M fund can be harder than $100M+

31:27 – The “sweet spot” for funds: $50–150M at fund three

34:40 – Shifts in management fees, carry, and LP negotiations

39:51 – The rise of algorithmic VC funds and AI-powered due diligence

43:42 – Are large VC teams obsolete in the age of AI?

46:18 – Automating deal screening and data rooms with AI agents

50:19 – Back-testing with AI: learning from startup successes and failures

53:47 – How AI accelerates both VCs and founders

54:47 – Fees vs. carry: what LPs really want

57:48 – Strategies for liquidity, secondaries, and returning capital to LPs

01:01:05 – Europe vs. U.S. venture ecosystems post-2023 reset

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Arian Ghashghai is the Founder and Managing Partner of Earthling VC, a pre-seed venture fund focused on frontier technologies like VR, robotics, and applied AI. Previously, he was a senior ML engineer at Meta’s Reality Labs and an active angel investor, building a reputation as a thoughtful advocate for probabilistically diversified pre-seed investing. With his blend of technical expertise, founder experience, and sharp perspective on venture dynamics, he offers rare insights into how early-stage investing really works.

In this episode, Arian shares his unconventional path—from growing up as an immigrant in the U.S., to building startups, to becoming an investor shaping the future of frontier tech. His candid reflections on risk, fund mechanics, and why diversification beats the “great picker” myth make this conversation a must-listen for founders and investors alike.

In Today’s Episode We Discuss:

00:01 – Arian’s early life: moving from Germany to the U.S., first ambitions, and being raised by entrepreneurial parents

03:20 – Childhood lessons from financial volatility and how it shaped his drive for stability

10:40 – College at Georgetown: starting in business school, discovering coding, and launching a music-tech startup

16:30 – Dropping out to pursue a startup full-time, lessons from failure, and returning to complete his degree

22:00 – Joining Facebook/Meta: tackling misinformation, then moving into Oculus and AR/VR development

28:30 – First steps into angel investing while at Meta and discovering a passion for startups

35:00 – Becoming “the VR investor” and earning credibility with founders and fellow VCs

39:25 – Why Arian chose to launch Earthling VC instead of joining an established fund

46:00 – The fundraising journey: early struggles, securing an anchor LP, and defining the “why now”

53:00 – Why small, truffle-hunting funds succeed while mid-sized funds face existential risk

01:01:00 – Fund mechanics: Earthling VC’s $5M pre-seed strategy, check sizes, and portfolio design

01:03:30 – Why probabilistic diversification beats concentrated bets in pre-seed venture

01:13:00 – Debunking the “great picker” myth: why venture success is statistical, not magical

01:16:09 – The fragility of startups, black swan founder events, and why more shots on goal matter

Subscribe on Spotify: https://open.spotify.com/show/6Ga6v0YUsHotLhjap67uu5

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Dmitry Karpov is the CEO and co-founder of WorkDone, a real-time AI compliance co-pilot for hospitals tackling costly and often hidden documentation errors that lead to denied insurance claims. A two-time YC founder, ex-EY innovation leader, and Forbes Cloud 100 rising star, Dmitry brings deep experience in workflow automation and enterprise AI. With a track record of scaling companies globally and navigating highly regulated industries, he offers sharp insights into the intersection of healthcare, compliance, and AI-driven transformation. In this episode, he shares his entrepreneurial journey from a small scientific town in Russia to building cutting-edge healthcare AI, and the lessons learned along the way.

In Today’s Episode We Discuss:

00:01 – Meet Dmitry Karpov

00:48 – Early Entrepreneurship in Russia

03:40 – Lessons from a Teenage Side Hustle

05:10 – From Physics to Startups

07:30 – Breaking into Corporate Innovation

09:40 – Founding Electronique

12:35 – A Strategic Exit and a New Focus

13:43 – Early Customer Development for WorkDone

15:50 – Why Denied Claims Are a $70B Problem

23:31 – Patient Lawsuits and Compliance Risks

27:18 – Manual Audits vs. AI Oversight

30:25 – Fighting False Positives in AI Compliance

35:27 – Selling into Hospitals

39:53 – Why Now Is the Right Time for Real-Time Compliance

43:15 – Running WorkDone on Dmitry’s Own Records

44:31 – Fundraising Lessons from Two YC Batches

46:55 – The First Clinic Visit

50:18 – Regulatory Acronyms and Compliance Jargon

51:05 – HIPAA vs. SOC 2

Subscribe on Spotify: https://open.spotify.com/show/6Ga6v0YUsHotLhjap67uu5

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Jay Levy is the co-founder and partner at Zelkova Ventures, an early-stage venture capital firm with over 17 years of experience backing transformative SaaS companies like Help Scout, Klout, and Crimson Hexagon. From designing websites in high school to scaling startups during the dot-com boom, Jay has lived the full founder-to-investor journey. With a disciplined, people-first approach to investing, he offers sharp insights on scaling efficiently, founder self-awareness, and how AI is reshaping the venture landscape.

In this episode, he discusses how to identify the right founders, lessons from startup failures, valuation discipline, and why the VC industry may need to reinvent itself in the AI era.

In Today’s Episode We Discuss:

00:01 – Welcome & Jay Levy Introduction

00:44 – Early days: building websites in high school

02:02 – Recurring revenue lessons from hosting clients

02:30 – First big project: city youth website gains national attention

03:55 – Joining Uconnections during the dot-com boom

04:48 – Startup collapse and lessons from scaling too fast

06:14 – Transition to Morgan Stanley and corporate reality check

07:15 – Leaving Wall Street for entrepreneurship

08:14 – Early days of New York’s tech scene

09:08 – Founding Zelkova Ventures and initial clean tech focus

10:46 – Lessons from Uconnections and the importance of pacing growth

12:43 – Finding a sustainable revenue model early

14:23 – How Zelkova’s investment thesis evolved

16:45 – The importance of valuation discipline

18:43 – Easy “no” deals and founder self-awareness

20:24 – Assessing the “ego-to-ability” ratio

21:23 – The three types of investors founders meet

23:37 – Avoiding investor-founder misalignment

24:47 – Zelkova’s check size and barbell investment approach

26:29 – Reserve strategy and follow-on investments

27:24 – Board observer seats vs. board member roles

29:15 – Managing multiple board observer roles

30:54 – How AI is reshaping product development costs

33:12 – From MVP to “Pretty Good Viable Product” with AI

34:41 – Building companies more efficiently with AI tools

36:10 – Could AI reduce the need for early-stage VC?

38:36 – Platforms, scalability, and AI’s “last mile” problem

40:29 – The shift toward AI-powered business operations

41:42 – Early-stage investment focus areas today

46:26 – In-person vs. remote-first startups

48:13 – Patterns of the best founders Jay has backed

50:58 – Where promising founders fall short

52:38 – The early-stage metrics that actually matter

54:58 – Why CAC and early-stage NPS are overrated

56:11 – Underappreciated metrics: qualitative customer feedback

57:57 – A company Jay passed on but still thinks about

59:11 – When valuation discipline pays off (and when it doesn’t)

01:01:13 – Being both a GP and LP in the venture world

01:03:00 – Later-stage investments for faster liquidity

01:05:41 – Thoughts on SAFEs, convertible notes, and doing it right

01:09:00 – Closing thoughts and where to connect with Jay Levy

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Greg Weinger is the Senior Vice President of Product Management at SheerID and the creator of The Powerful Introvert podcast. With over 15 years of experience scaling B2B SaaS product teams at companies like Urban Airship, YesMail, and Jive Software, Greg brings a unique blend of technical depth, leadership insight, and introverted clarity to every role he takes on. In this episode, he shares lessons from building enduring product orgs, thriving as an introvert in high-stakes environments, and shaping the future of identity verification.

In Today’s Episode We Discuss:

00:01 – Welcome & Guest Intro

00:50 – Building Product Teams That Scale

05:08 – Mentoring & Giving Feedback

06:23 – From English Major to Tech Leader

10:09 – What Makes SheerID Different

11:30 – The Complexity of Global Verification

12:46 – Balancing the Roadmap

15:50 – Communicating Product Vision

17:15 – AI in Product Management

19:36 – Engineering to Strategic Leadership

22:08 – Starting The Powerful Introvert

25:44 – Introverts vs. Extroverts

29:21 – Beyond Shyness

31:03 – Inclusive Meeting Design

34:36 – Future of Identity Verification

36:05 – The Future of Product Roles

37:37 – Knowing Product-Market Fit

39:21 – Scaling Product Lines

40:43 – Rapid Fire: Underrated PM Trait

41:51 – Favorite Enterprise Product

44:30 – Hardest Product Launch

46:55 – Disagreeing with Product Philosophies

48:30 – Book Recommendation

49:49 – Product-Market Fit Mistakes

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Chris Anzalone is the founder and CEO of Knowledge, an AI-driven sales intelligence startup reshaping the way businesses identify in-market buyers. With a unique background in high-ticket finance and agency sales, Chris bootstrapped Knowledge from a services-based business into a fast-scaling SaaS company, reaching thousands of users and notable ARR growth. In this episode, he shares how data, psychographic matching, and real human connection are unlocking the next frontier of outbound sales.

In Today’s Episode We Discuss:

00:01 – Intro & Background

02:00 – Wall Street to Sales Agency

04:40 – The CMO Dinner That Changed Everything

06:30 – Building the First Predictive Model

08:00 – Psychographic Matching & Neural Match

09:20 – Exiting the Agency, Entering SaaS

11:15 – Using Knowledge to Sell Knowledge

13:30 – Breaking Through with PLG

15:00 – Case Study: 26 Deals from 5,000 Emails

17:00 – Real-Time Data & Slack Alerts

20:00 – Onboarding & Personalization Engine

23:00 – Individual vs. Account-Based Intent

24:00 – Bootstrapping with Personal Capital

27:00 – Co-Founder Equity & Ownership

30:00 – ZoomInfo, Frenemies & Market Friction

33:30 – PLG Growth Inside Enterprises

34:10 – Pricing & “Guerilla Pilots”

36:00 – Broader Use Cases Beyond Sales

37:30 – AI SDRs vs. Human Connection

42:00 – Lessons from Exit #1

44:00 – Strategic Fundraising & Skipping Seed

47:30 – The Role of the Human in AI Sales

51:20 – Cold Outreach & Cobra Kai Story

52:30 – Most Underrated Sales Tactic

56:00 – Who’s Flying Blind on Buyer Intent?

58:33 – Wrap-Up

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