Frank Growth

Episode #211: Elia Wallen — Building a $2B travel platform by serving SMBs

How a founder built a multi-billion dollar company in an overlooked market.
For operators deciding whether to chase hype markets or serve ignored customers.

Elia Wallen is the founder and CEO of Engine, a business travel platform that grew out of his earlier company Travelers Haven. What started as a corporate housing service expanded after customers repeatedly asked his team to book hotels for traveling workforces. Looking closer revealed a gap between consumer OTAs and enterprise travel management companies that left SMB travel largely unmanaged. In this episode, Elia explains how Engine built a $2B+ company by focusing on SMB customers, running high-touch outbound sales, and staying disciplined on capital while competitors raised and spent aggressively.

What you’ll hear

• Why SMB travel was a large but ignored market between OTAs and enterprise TMCs
• How Engine built growth through outbound “smile and dial” sales to smaller businesses
• What broke when Engine expanded from hotels into flights and cars
• Why Elia turned down additional capital and avoided hiring a traditional CMO

Chapters

• 00:00 — Finding an overlooked gap in business travel
• 02:30 — From Travelers Haven to Hotel Engine
• 03:41 — Why SMB travel stayed unmanaged
• 04:16 — Building an outbound sales motion for SMBs
• 06:25 — Expanding from hotels to flights and cars
• 08:18 — Why Engine took less capital than it was offered

Links & resources

Guest
Elia Wallen — Founder & CEO, Engine
Engine website

Mentioned
Engine new customer offer — $250 off when you mention “Frank Growth” to your account executive

About Frank Growth

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions.
Hosted by Jason Shafton.

Promotional links

• Work with Winston Francois: https://wf.team/podcast
• Subscribe / Follow Jason: Jason Shafton on LinkedIn

Product marketing only matters if it changes pipeline, adoption, or retention.
This episode is for founders, PMMs, and operators trying to make product marketing actually impact growth.

Seif Salama joins Jason Shafton to break down what product marketing really does when it works. Seif has led product marketing across companies like Google, Fanatics, Carta, and AngelList, operating at both massive scale and early-stage startup speed. The conversation focuses on the real job of product marketing: translating product truth into market truth and helping customers understand and decide—not just creating decks or launch messaging. Seif explains how positioning should be rooted in customer language, why most sales enablement content fails, and how product marketing should influence (but not own) pricing, packaging, and product decisions.

• Why great product marketing translates “product truth” into “market truth”
• How positioning fails when it isn’t rooted in real customer language
• Why one-pagers don’t close deals—and what sales teams actually need instead
• How to measure product marketing when attribution is messy

Timestamped chapters

• 00:00 — Why sales enablement one-pagers don’t close deals
• 01:50 — What product marketing actually does
• 03:15 — What separates revenue-driving PMM from slide factories
• 04:08 — How positioning works (and how to test if it’s differentiated)
• 06:42 — How great product launches are structured
• 11:35 — What sales enablement actually means in B2B
• 15:48 — Measuring product marketing impact
• 19:16 — What PMMs should do in their first 90 days

Guest
Seif Salama — Product Marketing Leader
LinkedIn

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions.Hosted by Jason Shafton.

• Work with Winston Francois
• Subscribe / Follow Jason

How to design data systems that actually drive business outcomes.
For operators building analytics, loyalty, or AI initiatives under real constraints.

Pat Ryan, with experience at Discover, Organizing for Action, and United Airlines, joins Jason to break down what “data systems designed for growth” actually means in practice. They discuss infrastructure decisions that last decades, why loyalty programs are fundamentally data engines, and how United leaned on its loyalty program during the pandemic when flying stalled. Pat explains the difference between rewards and true loyalty, why most AI initiatives fail the path-to-value test, and what his first 90 days look like inside a growth-stage company.

• Why every data investment needs a clear path to value
• How loyalty programs move customers up the value chain
• Where data systems break: infrastructure decisions that outlive you
• A practical 90-day plan: process first, then goals, then people, then strategy

Timestamps from transcript.

• 00:00 — Why data only matters if it drives value
• 02:13 — Designing systems for commercial outcomes
• 03:50 — Infrastructure risk and long-term tech decisions
• 05:52 — Loyalty vs. rewards: data vs. discounting
• 10:08 — Why data trust is cultural, not technical
• 14:22 — AI hype vs. real path to value

Guest
Pat Ryan — United Airlines
LinkedIn

Mentioned
Databricks

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions.
Hosted by Jason Shafton.

• Work with Winston Francois
• Subscribe / Follow Jason

Outbound email is an impression now—not a response channel.
For seed to Series C revenue leaders building a real funnel and motion.

Lindsay Crittendon (CRO, Taylor Bird) breaks down how to build revenue strategy that persists—grounded in how customers actually use your product, not heroics. She explains why the first diagnostic is retention and product usage, why most “can’t close” problems are positioning problems, and how to define a real ICP that’s clear enough to make your CEO uncomfortable. You’ll also hear her decision rule for go-to-market motion (match price and buyer behavior), why founders own sales until $1–$2M in revenue, and how to design simple comp plans that don’t bankrupt you—starting with budgeting 20% for commissions.

• How to diagnose revenue: product usage/retention first, then positioning, then conversation quality
• How to define a real ICP (including a focused 500–600 company target list) and why focus beats “TAM”
• Why cold outbound email is mostly broken—and how to treat it as impressions instead of expecting replies
• How to pick PLG vs sales-led vs hybrid based on willingness to pay, and when to hire your first AE

Chapter topics (no timecodes).

• 00:00 — Why outbound is broken and email is just an impression
• 02:18 — Revenue strategy: persistent money over time (not heroics)
• 02:48 — What teams overlook: post-sale truth, customer usage, and what customers care about
• 04:16 — Diagnosing a revenue org: retention, positioning, and conversation quality
• 05:52 — ICP discipline: make it small, specific, and repeatable
• 07:11 — Choosing the right motion: match price and buyer behavior (PLG vs sales-led)
• 09:21 — Outbound today: stop expecting replies; use it for cheap impressions
• 10:25 — Minimum viable sales process: founder-led until ~$1–$2M
• 11:55 — Hiring and comp: budget 20% for commissions and keep plans simple
• 14:31 — Sales + marketing operating rhythm: partnership, respect, and shared accountability
• 16:23 — Speed round: product usage, discovery questions, stalled deals, and picking up the phone
• 17:15 — Building momentum: “what’s the first thing we can do together?” (mutual NDA example)
• 18:07 — Turnarounds: proving lost PMF with data, then fixing product and positioning
• 19:39 — Where to find Lindsay and what to reach out about

Guest
Lindsay Crittendon — CRO, Taylor Bird

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions. Hosted by Jason Shafton.

• Work with Winston Francois
• Subscribe / Follow Jason

How to design events where the right people actually meet and follow through.
For founders and operators building communities, networks, or community-led growth.

Kushagra Shrivastava is a builder and community investor behind Zoogler, a 40,000+ ex-Google alumni network. He explains how he defines “serendipity” as structured randomness within constraints, how he measures it through behavioral signals (like connection velocity), and what he considers non-negotiable when hosting events. We also cover why Zoogler outgrew a stack of tools like Google Sheets, Airtable, and Eventbrite-style platforms, what changed during the 2023 Google layoffs, and how his product Key uses intent to drive warm introductions for outcomes like hiring, fundraising, and business development.

• A practical definition of serendipity, “structured randomness within constraints,” plus how to measure it
• The 3 non-negotiables for events: pre-event intent collection, designed “collision moments,” and forced closure with a next step
• What breaks communities: optimizing for quantity (content and connections) instead of intent and outcomes
• A founder checklist for starting a community as an individual vs. as a brand and how to scale once you know what works

If transcript includes timestamps, use mm:ss or hh:mm:ss.

• 00:00 - Defining serendipity and how to measure it
• 06:20 - Zoogler overview: building a 40,000+ ex-Google network
• 07:18 - Minimum viable magic for events: intent, collisions, forced closure
• 09:32 - Key: turning intent into warm intros and outcomes
• 14:32 - Founder checklist: building community as a person vs. a brand
• 17:35 - Lightning close: the one takeaway

Guest
Kushagra Shrivastava - Builder and community investor (Zoogler; Key)

Frank Growth is a podcast about how companies actually grow, real operators, real constraints, real decisions.
Hosted by Jason Shafton.

• Work with Winston Francois: https://wf.team/podcast
• Subscribe / Follow Jason: https://www.linkedin.com/in/jasonshafton/

How to design events where the right people actually meet and follow through.
For founders and operators building communities, networks, or community-led growth.

Kushagra Shrivastava is a builder and community investor behind Zoogler, a 40,000+ ex-Google alumni network. He explains how he defines “serendipity” as structured randomness within constraints, how he measures it through behavioral signals (like connection velocity), and what he considers non-negotiable when hosting events. We also cover why Zoogler outgrew a stack of tools like Google Sheets, Airtable, and Eventbrite-style platforms, what changed during the 2023 Google layoffs, and how his product Key uses intent to drive warm introductions for outcomes like hiring, fundraising, and business development.

• A practical definition of serendipity, “structured randomness within constraints,” plus how to measure it
• The 3 non-negotiables for events: pre-event intent collection, designed “collision moments,” and forced closure with a next step
• What breaks communities: optimizing for quantity (content and connections) instead of intent and outcomes
• A founder checklist for starting a community as an individual vs. as a brand and how to scale once you know what works

If transcript includes timestamps, use mm:ss or hh:mm:ss.

• 00:00 - Defining serendipity and how to measure it
• 06:20 - Zoogler overview: building a 40,000+ ex-Google network
• 07:18 - Minimum viable magic for events: intent, collisions, forced closure
• 09:32 - Key: turning intent into warm intros and outcomes
• 14:32 - Founder checklist: building community as a person vs. a brand
• 17:35 - Lightning close: the one takeaway

Guest
Kushagra Shrivastava - Builder and community investor (Zoogler; Key)

Frank Growth is a podcast about how companies actually grow, real operators, real constraints, real decisions.
Hosted by Jason Shafton.

• Work with Winston Francois: https://wf.team/podcast
• Subscribe / Follow Jason: https://www.linkedin.com/in/jasonshafton/

Episode #206: Steve Dennis — How to Write Like a Human in the Age of AI

AI can generate endless copy. The new bar is making someone feel something.
This episode is for founders, marketers, and anyone who writes for a living and wants their work to connect.

Steve Dennis is a writer and ghostwriter who has shaped voices the world knows—including Andy Puddicombe at Headspace. Jason and Steve go back to the Headspace days, where Steve helped define the brand voice and coached writers (including Jason) on how to sound human on the page. In this conversation, they cover how to capture someone else's voice authentically, why vulnerability makes writing believable, and what AI still can't replicate.

What you'll hear

• Why your spoken word is where authenticity lives—stop "writing" and start speaking your story first
• The ghostwriter's test: can your closest friends read it and think it's your voice?
• What AI gets wrong: it engineers patterns, not meaning—it has no conscience, memory, or imagination
• The "remembering room" technique for evoking sensory detail and emotional truth

Chapters

• 00:00 — Cold open: Writing about mistakes is writing about being human
• 00:33 — Opening riff: Three traps of AI-era writing
• 02:33 — Steve's background and working with Andy Puddicombe
• 05:16 — How to disappear as a ghostwriter
• 07:27 — The biggest authenticity mistake: putting a dinner jacket on language
• 10:06 — The irreplaceable role of human writers
• 13:13 — Why AI can't access your memory bank
• 15:03 — Book recommendations: Stephen King and Robert McKee
• 17:38 — Where to find Steve and closing

Links & resources

GuestSteve Dennis — Writer
Twitter/X
InstagramAgency: Curtis Brown (London)

Mentioned
"On Writing" by Stephen King
"Story" by Robert McKee

About Frank Growth

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions. Hosted by Jason Shafton.

Promotional links

• Work with Winston Francois
• Subscribe / Follow Jason

Episode #205: Jordan DiPietro — How to Turn an Audience Into a Community That Compounds Growth

Most companies stop at audience. This episode shows you how to build community that creates its own pipeline.
For founders and operators who want retention, not just reach.

Jordan DiPietro has built audience-to-community flywheels at The Motley Fool, The Hustle (inside HubSpot), and as CEO of Hampton. In this conversation, he breaks down the specific systems Hampton used to vet members—including raising the revenue threshold from $1M to $3M and personally reviewing every applicant video. He explains why trust compounds through radical transparency (like publishing every stock pick, good and bad, at Motley Fool) and how to pick a content medium you won't burn out on.

What you'll hear

• The difference between audience and community: if the party stops when you leave, you don't have a community
• How Hampton's vetting process filtered for members who give more than they take
• Why founder-as-creator is really about distribution, not personal branding
• The SVB crisis moment when Hampton's community self-organized faster than the company could respond

Chapters

• 00:00 — Cold open: Audience vs. community defined
• 00:27 — Introduction and Jordan's background
• 01:13 — The through-line: audience → trust → community
• 03:33 — Hampton's depth-over-breadth systems
• 05:15 — Founder's arbitrage: attention, trust, and taste
• 06:27 — SVB crisis: community self-organizing in real time
• 07:49 — Why founder as creator is no longer optional
• 09:32 — Minimum viable cadence for content creation
• 10:48 — Start with community from day one
• 11:55 — One operating principle for durable growth
• 13:11 — Where to find Jordan
• 13:52 — Closing takeaways

Links & resources

GuestJordan DiPietro — ex-CEO of Hampton, former leader at The Hustle (HubSpot) and The Motley Fool
Website / Newsletter (Signal Noise)

Mentioned

Hampton

The Hustle

The Motley Fool

About Frank Growth

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions. Hosted by Jason Shafton.

Promotional links

• Work with Winston Francois
• Subscribe / Follow Jason

Episode #204: John Kennelly — Founders who hate sales still have to sell

If sales feels intrusive, this episode reframes it as problem-solving.
Built for founders avoiding sales calls, decks, and outreach.

John Kennelly, Founder of I Hate Sales, works with founders who have never had a sales job and actively avoid selling. In this episode, he explains why sales fear is usually a mindset problem, not a skill gap, and why curiosity matters more than persuasion. The conversation covers running discovery without pitching, qualifying people out quickly, and why early founders slow themselves down by building systems instead of talking to customers. Kennelly shares concrete examples from his cohort work, including starting with interviews instead of sales calls and what to track before using a CRM.

What you’ll hear

• Reframing sales from “intrusion” to helping through discovery
• How to run interviews instead of sales calls
• Why broad ICPs, decks, and CRMs backfire early
• The only two metrics to track before you have customers

Chapters

Chapters with timestamps

• 00:00 — Why founders dread sales
• 02:17 — Sales as helping, not intruding
• 03:39 — Curiosity and discovery before pitching
• 05:17 — Qualifying hard and knowing your ICP
• 08:16 — Interviews instead of sales calls
• 13:48 — What to track before using a CRM

Links & resources

GuestJohn Kennelly — Founder, I Hate Sales
Website
LinkedIn

About Frank Growth

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions. Hosted by Jason Shafton.

Promotional links

• Work with Winston Francois
• Subscribe / Follow Jason

How founders use acquisitions to grow without betting the company.
For operators considering their first inorganic deal.

Trevor Houghton is CEO of Pass Galleries and a former private equity and corporate development operator. He breaks down how founders can use acquisitions to increase enterprise value without overextending capital. The conversation covers how deals actually get sourced, why most failed acquisitions start with the wrong premise, and how Trevor structures transactions using debt, seller notes, and earn-outs to reduce downside. He walks through a concrete example of acquiring $5M in EBITDA with no net cash outlay and explains why integration planning must start before the deal closes.

• Why the best acquisitions start as partnerships, not cold offers
• The customers vs. capabilities rule and why you must only extend one
• How no-money-down deals work using debt and deferred payments
• Why day-one integration and early culture alignment determine outcomes

Timestamps derived from the episode transcript.

• 00:00 — Structuring acquisitions with minimal cash risk
• 00:30 — Introduction to inorganic growth and Trevor’s background
• 01:44 — Building acquisition paths through partnerships
• 03:13 — The customer vs. capability decision framework
• 04:07 — Identifying targets through existing customer usage
• 05:03 — Growing earnings and valuation through acquisitions
• 06:04 — Integration planning before close
• 06:29 — Culture integration and no-money-down deal mechanics
• 08:05 — Building an acquisition engine

Guest
Trevor Houghton — CEO, Pass Galleries
https://www.linkedin.com/in/trevor-houghton-th/

Frank Growth is a podcast about how companies actually grow—real operators, real constraints, real decisions.
Hosted by Jason Shafton.

• Work with Winston Francois: https://wf.team/podcast
• Subscribe / Follow Jason: https://www.linkedin.com/in/jasonshafton/