Adam O'Donnell

Sit Down Startup

Business EN ↓ 105 episodes

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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Author

Adam O'Donnell

Category

Business

Podcast website

listen.casted.us

Latest episode

Feb 12, 2025

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Episodes

Bootstrapped to $40M and then raised $125M? Slice’s Founder, Ilir Sela 04.10.2023

Join us for the latest episode of Sit Down Startup! Anyone want to order a pizza? You're in luck. This week's guest Ilir Sela is the founder and CEO of Slice, a platform that "builds innovative tech to empower America’s independent pizzerias." Sounds delicious! Ilir dives into... Fax-machine-MVP - meet the customer where they are Why he bootstrapped to $40M GMV vs. raising sooner What he looked fo...

[$150M raised] OpenStore’s Co-Founder, Jeremy Wood: Building the Right Engine: Overcoming Doubts 06.09.2023

Jeremy Wood's solution, OpenStore, offers these founders the option to sell their businesses or have OpenStore operate and run the stores on their behalf. This innovative approach has not only provided a lifeline for many e-commerce founders but has also positioned OpenStore as a major player in the e-commerce market. Join Adam O'Donnell and Jeremy Wood as they delve deeper into this topic on the...

[$200M+ Raised] Self-Doubt & Worry to Thriving Through Startup Challenges; Electric.ai's Founder, Ryan Denehy 24.08.2023

Ryan Denehy discussed the importance of overcoming self-doubt in the early stages of a startup. He shares his own experiences, practical advice, and data-driven insights that can help founders navigate the competitive business landscape. Thank you to this week's partners Aktie Now and WorknetGPT! Aktie Now has a special offer for startups joining the Zendesk for Startups program: Zendesk Express i...

The Founder-led Content Formula; Atrium’s Founder Pete Kazanjy 09.08.2023

Atrium, a software company co-founded by Pete Kazanjy in 2016, has achieved more business success with fewer Sales Development Representatives (SDRs). This accomplishment can be credited to their strong inbound game and their valuable content that educates and provides insights to their community of 35,000 members.  Atrium's software helps businesses implement data-driven sales management by monit...

[$1.2B Val] Epidemic Sound's Founder, Oscar Hoglund: Overcoming Gov Regulations & Launching A Marketplace 26.07.2023

The success of Epidemic Sound, a platform for content creators and music artists, is a testament to the skill, and creativity of Oscar Hoglund and his team. Despite the numerous legal and financial obstacles they encountered, they refused to give up on their mission and took the fight to Brussels to change copyright laws and protect artists from exploitation. The key to their success was their pas...

Tailscale's $113M Success: Developer-Led-Growth 14.07.2023

Tailscale has been a huge success, raising over $113 million and growing to 80 employees. They discovered that if developers love the product, they will tell their decision makers in their organization to buy it, and the money will follow. To ensure customer satisfaction, they use Net Promoter Score to move people from the middle to the top and offer free support for everyone, even those on the ze...

[$161M Raised] From Series A Struggles to 400 Employees: LinkSquares' Growth Strategies with Founder Vishal Sunak 21.06.2023

Vishal Sunak, Founder of LinkSquares, shares his journey of building software for legal teams. Listen as he speaks to Sit Down Startup's host Adam O'Donnell about raising $161 million over five rounds of venture capital, overcoming fundraising struggles, and unlocking the secrets to growth.  Discover the importance of building a strong product, founder-led sales, and knowledge assembly, as well as...

Bootstrapped to $100M+ Exit: Pardot’s Founder, David Cummings' Startup Journey 07.06.2023

Join Adam O'Donnell on Sit Down Startup as he sits down with David Cummings, the founder of Pardot, which eventually sold to Salesforce. In this episode, they discuss pivoting from unsuccessful strategies, customer discovery, and marketing automation platform, while sharing their personal stories of startup challenges.

Instacart's Former Chief Growth Officer; Building a Successful ML Startup: Anomalo's, Founder, Elliot Shmukler 24.05.2023

Adam O'Donnell sits down with Elliot Shmukler, former Chief Growth Officer at Instacart and co-founder of Anomalo, to discuss the challenges data teams face in detecting and solving data quality issues using machine learning. Despite the initial failure of their product to meet customer needs, Anomalo was able to grow 10x ARR during the big recession by listening to customer feedback and building...

$0 to 100M ARR in 18-months: Revolutionizing Cloud Security With Base Thinking; Wiz’s Co-Founder, Ami Luttwak 10.05.2023

Welcome to the Sit Down Startup podcast, where host Adam O'Donnell interviews entrepreneurs and startup founders about their inspirational stories. In this episode, Adam brings in Ami Luttwak, the CTO and co-founder of Wiz , one of the largest cloud security companies. Ami shares the hands-on culture of the company, where all managers do the work themselves, and explains how they identified a gap...

($155M raised) Glean’s Founder, Arvind Jain: How to close enterprise deals from day one 26.04.2023

Glean was founded in 2019 as an AI-powered workplace search engine aimed at helping people browse through their company apps to find the information they need and boost productivity. Since then, Glean has raised $155M+ and grown to 200+ employees while staying true to its initial mission. In this episode its founder, Arvind Jain, shares his experience and provides a few key insights: Ask the hard...

Bootstrapped to nearly $100M exit to Citrix; Jesse Lipson; knowing when to ignore the “smart” advisors vs. just building 29.03.2023

Jesse Lipson initially thought he would become a philosophy professor — until he took a job with a startup that changed his career path. After founding his first company Sharefile in 2005, he sold it to Citrix in late 2011 for almost $100M. And in October 2017 he established Levitate, which helps relationship-based businesses keep in touch with clients in a more personal and authentic way. This en...

[$271M raised] Frubana’s Founding Engineer, now board member, Daniel Bilbao; GTM tactics for $0 - $1M 22.03.2023

During Truora’s first year, they raised no money. Four years later, this customer-engagement and WhatsApp-first startup has come a long way, with 8M USD in ARR, 14M USD in revenue, and presence across seven Latin American countries. Co-Founder and CEO Daniel Bilbao shares his tips for founders looking to succeed:   Hire the best people you can. Talent comes first; good recruiting never fails. Do t...

Backed by a16z, Virtually Human Studio’s Co-Founder, Chris Ebeling: Building with community, listening vs. letting them lead 08.03.2023

When Chris Ebeling co-founded entertainment company Virtually Human back in 2018, Blockchain was just becoming popular. Since then, the company has raised $21M+ and their online horse racing game ZED RUN gained an impressive following.  In this episode, Chris talks to Adam about his experience launching in the digital world and shares a few tips:   Innovation comes with risks. Don’t be afraid to s...

Zapier’s Founder: scalable growth strategies 01.03.2023

Zapier has one mission: to help companies use automation to connect tools and apps so data can automatically move between them. The business was founded in 2012 and their remote team has since expanded worldwide across 40 countries. Founder Mike Knoop shared some takeaways from their 11-year journey so far: Stay patient. Growth is organic, so be prepared to play the long game. Tap into search. Cre...

[$0 - IPO] Braze’s Founder, Mark Ghermezian; knowing when to pivot & the power of persistence 22.02.2023

Back in 2008, when mobile apps were the talk of the town, Mark Ghermezian had an idea: build a bridge between app developers and users. That was the seed for Braze, a customer engagement platform, which has grown to 1200+ employees and 3.5M+ monthly active users.  In this episode, Mark tells his story and teaches us a few lessons: Iteration is key. Listen to feedback from designers and people usin...

Talkdesk & Cleverly Co-Founder: Cristina Fonseca - Product obsessed, 5-min rule & not being distracted by competition 15.02.2023

Cristina Fonseca, our very own VP of Product, knows a thing or two about being a founder. She has set up two companies specializing in CX: Talkdesk, back in 2011 (right after college!), which went on to raise over 250M USD; and Cleverly in 2017, now acquired by Zendesk.  In this one-to-one with Adam, she shares her experience:  Build trust. Stay present and proactively communicate with your custom...

[$396M Raised] Nailing pitch-market-fit? Eightfold AI’s CEO, Ashutosh Garg 09.02.2023

When Ashutosh Garg founded talent intelligence platform Eightfold AI in 2016, he had one clear goal in mind: to help businesses hire and retain the best professionals out there. The company has since grown to almost 700 employees and has raised $400M. Ashutosh sat down to discuss Eightfold’s journey with Adam, sharing a few learnings along the way: Strike the right balance. Both a lack of and over...

[0-IPO] Yext’s Founder, Howard Lerman: key to building a lasting company 25.01.2023

Howard Lerman founded tech company Yext in 2006, recording revenues of $100M during his final quarter as CEO. In November 2022, he started building his next project: Roam, an all-in-one Cloud HQ — and predicts it’s going to be even bigger.  The entrepreneur joined Adam for a chat to share some key insights and strategies from his +20 years’ experience:  Make customers love you. Happy clients will...

[$0-IPO] Shift’s Co-Founder, Toby Russell; knowing when to pivot DESPITE having product-market-fit?! 16.11.2022

In 2013, e-commerce platform Shift set out with one simple mission: to make car sales and purchases a seamless experience. The company began accelerating in late 2015 before they went public in 2020, and last year recorded revenues of 630M USD, selling vehicles in all 50 US states. Co-Founder Toby Russell joined Adam to share a few insights from their journey:   Keep it simple. When scaling, don’t...

[$99M raised] Sweep’s Co-Founder, Rachel Delacour; listening for low signals during customer research to land big logos 09.11.2022

Carbon emission tracking company Sweep was founded in June 2020. In just over two years, they have evolved to employ +80 people across Europe and the United States and, in less than 12 months, raised an impressive 100M USD. We sat down with Co-Founder & CEO, Rachel Delacour, who shared some key learnings:     Test your product with friends. Get in touch with past clients or contacts to present you...

[$600M+ raised] Deel’s Founder, Alex Bouaziz: pivoting with conviction 26.10.2022

Founded in 2019 with the goal of offering a simple solution for hiring freelancers and contractors internationally, Deel pivoted just a week before demo day. They restructured their program and grew to over 1,900 employees, 10K+ customers worldwide and raised $600M+.  Here are the key takeaways from our chat with Co-Founder & CEO, Alex Bouaziz: Time is money. Move fast and see what sticks — you ar...

[$1.6B val] Mercury’s Founder, Immad Akhund; rapid growth via word of mouth 19.10.2022

Mercury, a banking service for startups, was launched in 2019 but their business idea had been brewing since 2013. Mercury has now grown to 357 employees and tens of thousands of customers.  CEO & Co-Founder Immad Akhund joined us to share some advice:   Classic strategies work. Encourage your investors to talk about you on social media to get word-of-mouth going. Show ambition. Make sure your mes...

[$1.2B val] Pilot’s CEO, Waseem Daher; knowing where to stay in the weeds 12.10.2022

Founded in 2017, Pilot is a platform that offers bookkeeping, tax and CFO services for growing businesses. From a team of 10 to now 400, Pilot helps thousands of startups — crediting their speed, responsiveness and going above and beyond for customers as key to their growth. We sat down with CEO & Co-Founder, Waseem Daher, who shared his biggest takeaways:   Be ‘in the weeds’. Stay close to the de...

[Acquired by Apple] Beats by Dre’s Omar Johnson on building a brand and standing out 28.09.2022

In 2010, Beats by Dre saw a huge opportunity to pivot and make a mark. They were able to uniquely combine the world of sports and music in a way people hadn’t seen before. A clear vision and authentic messaging helped differentiate themselves.  We talked with former CMO, Omar Johnson, who shared insights from Beats’ early days:    Set clear objectives. Find an authentic place for your product.  Di...

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