Sit Down Startup – Details, episodes & analysis

Podcast details

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Sit Down Startup

Adam O'Donnell

Business

Technology

Frequency: 1 episode/16d. Total Eps: 105

Here’s how to startup. Even when the world goes topsy-turvy. From one home office to another, Zendesk leaders chat with founders, CEOs, and makers on their startup journey. There’s rule-flipping, new dogma and recycling failure into growth. Plus, why customer experience is at the heart of success, as told by people who know unpredictability inside out. (That seems pretty helpful right now.)

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🇨🇦 Canada - management
21/02/2026
#72

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https://www.zendesk.com/lp/startup-partner/?ref=gen&amp
37 shares
http://haveignition.com
2 shares
http://slack.com/promo/partner?remote_promo=1d1d4669
2 shares

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RSS feed quality

Good

Score global : 73%

Publication history

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[$10M+ Raised] Mark Doble, Co-Founder of Alexi, on Overcoming Adversity and Achieving Product-Market Fit in Legal Tech

Season 9 · Episode 3

Wednesday, February 12, 2025 • Duration 18:47

Welcome back to this week’s episode of Sit Down Startup! Today, host Adam O'Donnell sits down with Mark Doble, Co-Founder of Alexi, to explore his inspiring journey in the legal tech space and the challenges of achieving product-market fit while raising over $10 million in funding.

Join us as Mark shares his experiences transitioning from law to entrepreneurship, the pivotal moments that tested his resolve, and how Alexi is revolutionizing legal research through innovative AI solutions. He emphasizes the importance of conviction, adaptability, and understanding market needs in building a successful startup.

(00:00:00) The Low Points: Overcoming Adversity in the Early Days of Alexi

(00:03:40) From Law School to Startup: Finding the Path to Entrepreneurship

(00:09:23) The Turning Point: Achieving Product-Market Fit with Customer Validation

(00:15:40) First Principles Thinking: Innovating in Legal Tech Beyond Conventional Wisdom

Apply to the Zendesk for Startups program. Qualifying startups can use Zendesk for six months for free. Click to learn more: https://www.zendesk.com/lp/startup-partner/?ref=gen&partner_account=0016R00003GUn7OQAT

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[Harnessing AI Technology for Business Growth] Founder Daniel Saks Discusses Persistence, Overcoming Rejection, and the Evolution of AppDirect and Landbase

Season 9 · Episode 2

Wednesday, January 29, 2025 • Duration 22:23

In the latest episode of Sit Down Startup, Adam O'Donnell sits down with Daniel Saks, co-founder and CEO of Landbase, to delve into his entrepreneurial journey, including the successes and challenges he faced while building AppDirect. Daniel shares invaluable insights into the evolution of AppDirect, which has grown into a unicorn valued at over half a billion dollars, and how those experiences shaped his current venture, Landbase.

Discover the pivotal moments during the early days of AppDirect, including the struggle to achieve product-market fit and the lessons learned from facing rejection. Daniel discusses the transformative potential of agentic AI in generating predictable pipelines for businesses and how his team is working to address the pain points of lead generation for startups. Tune in for an engaging conversation about resilience, innovation, and the importance of maintaining conviction in your vision as a founder.

(00:00:19) The Early Entrepreneurial Spirit and Building AppDirect

(00:10:05) Overcoming Challenges on the Path to Product-Market Fit

(00:19:18) The Role of Agentic AI in Modern Business Strategies

(00:23:08) Insights on Conviction, Resilience, and the Future of Startups

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[$300M Raised] Mapping the Human Immune System for Drug Discovery: Noam Solomon on Building Immunai

Season 8 · Episode 26

Wednesday, August 28, 2024 • Duration 23:45

In this latest episode of Sit Down Startup, Adam O'Donnell chats with Noam Solomon, CEO of Immunai, about his incredible journey from academia to building a groundbreaking biotech startup. Hear Noam's fascinating backstory growing up in Israel and his move to the U.S. for a postdoc at MIT and Harvard, and how that paved the way for the creation of Immunai. Learn about the challenges of navigating product-market fit in the deep science space and the responsibility that comes with managing significant funding. Noam also shares insights on the crucial balance between building innovative technology and staying closely connected with customer needs. Tune in for an inspiring conversation on the future of drug discovery and the importance of humility in research and entrepreneurship.

00:01:49: Noam’s Academic Journey and Move to the U.S.
00:08:16: The Weight of Managing Large-Scale Funding
00:16:46: Balancing Innovation and Customer Feedback
00:19:26: Advice for Founders and Navigating Challenges

Apply to the Zendesk for Startups program. Qualifying startups can use Zendesk six months for free. Click to learn more: https://www.zendesk.com/lp/startup-partner/?ref=gen&partner_account=0016R00003GUn7OQAT

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Lemlist's Guillaume Moubeche and why CX is everyones job

Season 1 · Episode 5

Friday, July 24, 2020 • Duration 27:32

Lemlist is an email outreach platform helping sales teams, agencies, and B2B businesses stand out in a crowded inbox. Speaking across the pond, France-based CEO and Co-Founder, Guillaume Moubeche, is in conversation with Prelini Udayan-Chiechi, Zendesk’s VP of Marketing, EMEA in London. Together, they chat about:

- Prospecting techniques, and the “right time” to reach out—even during a pandemic

- The undervalued power of empathy in sales

- Aligning sales and support strategies

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Glofox’s Anthony Kelly on the rise of the Chief Customer Officer

Season 1 · Episode 4

Friday, July 24, 2020 • Duration 22:34

Anthony Kelly is the Co-Founder and Chief Customer Officer of Glofox, an intuitive gym management software solution, which enables entrepreneurs to grow their own fitness business. From his home office in Dublin, Anthony chats with Zendesk’s Chief Marketing Officer (and fitness lover), Jeff Titterton. They discuss delivering experiences in a shifting world, including:

- Anthony’s tried-and-tested motto: “When the customer wins, we all win”

- Why the virtual fitness format is here to stay

- How Glofox is evolving their customer base from boutique to enterprise gyms

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Tymeshift’s Elisa Reggiardo on the value of support leaders

Season 1 · Episode 3

Tuesday, June 30, 2020 • Duration 28:58

Tymeshift’s Chief Brand Officer, Elisa Reggiardo, sits down with Zendesk’s Senior Director of Content and Event Marketing, Sarah Reed. While continents apart, the pair catch up on:

Why support gets deprioritized by founders, and the power of support leaders driving efficient and engaged teams

The unique startup challenge: balancing team culture with growth and change

Making the most of workforce management solutions to build teams of all sizes

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Startup Grind’s Derek Andersen on virtual C2C strategy

Season 1 · Episode 2

Tuesday, June 30, 2020 • Duration 26:36

Derek Andersen is the Co-Founder and CEO of Startup Grind, a global community for educating and connecting entrepreneurs. He chats with Marcio Arnecke, Zendesk’s VP of Regional Marketing AMER, on the value of investing in community, especially in a post-COVID world.

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Aura’s James Gutierrez on empathy as secret sauce

Season 1 · Episode 1

Friday, June 26, 2020 • Duration 23:53

Aura Founder and CEO, James Gutierrez, sits down with Zendesk CFO, Elena Gomez, to share Aura’s mission to provide affordable, credit-building loans to working families in America. While pretending to sip cortados in a coffee shop, they chat:

James’s personal journey building Aura, and his motivation to open doors for low-income families
Adapting to COVID-19 by arming customers with “moral collateral”, making customer experiences more digital, and offering “pay what you can” options
Leading with compassion, and how empathy drives Aura’s startup culture—and success

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[90% of Co-Founder's Time Spent Speaking to Customers] How Inspectify has Navigated Startup Success

Season 8 · Episode 25

Wednesday, August 14, 2024 • Duration 20:27

Welcome to the latest episode of Sit Down Startup! This week Adam O'Donnell hosts Inspectify co-founder and CEO Josh Jensen who leverages his diverse background in engineering and real estate to revolutionize property inspections for single-family homes. Josh brings a unique perspective to the tech space, emphasizing the importance of capturing comprehensive home data to support decision-making. His journey, marked by early-stage company experiences and real estate investment, shaped his belief in the necessity of efficiency and transparency, especially in startup operations. Despite setbacks, Josh remains committed to iterating based on customer feedback and actively engaging in sales to ensure Inspectify meets market needs effectively.

(00:03:34) Navigating Layoffs: Lessons for Founders

(00:07:19) Iterative Evolution of Target Customer Fitting

(00:14:01) Direct Founder Sales Engagement for Startup Success

(00:18:24) Operational Success through Transparency in Startups

Qualifying startups can use Zendesk six months for free. Click to learn more: https://www.zendesk.com/lp/startup-partner/?ref=gen&partner_account=0016R00003GUn7OQAT

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[$0 to $20M ARR in 1 year] Creating a Path to Financial Empowerment with Brigit's co-founder and CEO Zuben Mathews

Season 8 · Episode 24

Wednesday, July 31, 2024 • Duration 25:21

Host Adam O'Donnell is back with this week's episode of Sit Down Startup with guest Zuben Mathews, co-founder and CEO of the financial health app Brigit. Mathews draws from his own experiences of financial hardship and his background in economics to address the critical issue of product-market fit in financial technology. He also emphasizes the importance of listening closely to the core pain points of customers, such as financial stress from living paycheck to paycheck, lack of credit score, and insufficient savings.

Learn more about how Mathews advocates for swiftly transitioning from extensive research to real-world testing, as real-world feedback offers invaluable insights that can refine and perfect the product. Moreover, the founder stresses the need for truly understanding market needs and gaining customer trust, seeing these as essential components for achieving product-market fit and creating impactful financial solutions that can alleviate financial stress. Stream the full episode now.

(00:08:15) Employee Job Security Amid Covid Crisis

(00:12:45) Data-Driven Overdraft Solution Development Journey

(00:16:24) User Engagement through Market Research for Growth

(00:20:41) Targeted Online Advertising for Financial Stress Relief

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Sit Down Startup – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

RSS feed quality and score

Publication history

Latest published episodes

Related Shows Based on Content Similarities

Apple Podcasts

Spotify

Related Shows Based on Content Similarities

Sit Down Startup – Details, episodes & analysis

Podcast details

Recent rankings

Apple Podcasts

Spotify

Shared links between episodes and podcasts

Other23

RSS feed quality and score

Publication history

Latest published episodes

Similar podcasts and content

Related Shows Based on Content Similarities

Apple Podcasts

Spotify

Related Shows Based on Content Similarities

Other23