The Grid is a podcast about email, communication strategy, the tech industry, and scaling your business. Tune in as SendGrid’s CMO Scott Heimes interviews our customers, our employees, and industry thought leaders.
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Sendgrid Podcasts
The Say Yes To Profits® Podcast is where consultants and coaches come to master their money and scale with confidence. Each week, Dr. Octavia Conner, award-winning Virtual CFO, Financial Strategist, and founder of Say Yes To Profits®, shares proven strategies to increase profitability, stabilize cash flow, and minimize taxes so you can grow your business without stress or uncertainty. More than a podcast about numbers, this is your roadmap to financial leadership. You will discover how to ma ...
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Some Coding Required is a podcast about all things open source. Hosted by Twilio SendGrid’s Senior Developer Experience Engineer, Elmer Thomas. Episodes will share answers to questions from the open source community, industry news, efficiency-focused hacks and apps, deep dives on open source topics, and more.
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Outsider Inc. is dedicated to visionary leaders breaking the mold of tech entrepreneurship. Hosted by Ian Hathaway—co-author of The Startup Community Way: Evolving an Entrepreneurial Ecosystem and co-founder of seed-stage venture capital firm FOVC—each episode delivers exclusive interviews and insider insights from exceptional founders building generation-defining companies. Join us for an in-depth exploration into the real-life stories of entrepreneurs from unexpected places and backgrounds ...
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In the startup world, Give First means simply trying to help anyone—especially entrepreneurs—with no expectation of getting anything back. It's the pay-it-forward principle that builds strong startup networks. Hosts David Cohen and Brad Feld—Techstars cofounders, lifelong entrepreneurs, and startup investors—talk with mentors and founders about what giving first looks like in action, and how it makes great entrepreneurship possible. Hosted on Acast. See acast.com/privacy for more information.
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Groundwork features Chief People Officers from the world’s fastest-growing companies. These leaders guide organizations through the turbulent times of hypergrowth by investing in human beings. They lay the groundwork that makes the impossible, inevitable. Join Lingo Live CEO Tyler Muse for conversations on how they became the leaders they are today, how they’ve navigated their toughest challenges, and how they envision the future of work.
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Dynamic Capitalism & Building Entrepreneurial Ecosystems Anywhere w/ Seth Levine, Co-Founder of Foundry
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56:16In this episode of Outsider Inc., host Ian Hathaway sits down with Seth Levine, co-founder and longtime partner at Foundry, to explore a two-decade journey at the center of entrepreneurship, venture capital, and ecosystem building outside traditional power centers. Levine reflects on helping build Foundry into a top-tier venture firm based in Bould…
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In this episode of the Give First podcast, David Cohen talks with Seth Levine, Partner at Foundry and co-author of Capital Evolution. Seth looks back on the early days of Techstars, the original Boulder community that shaped it, and how Foundry is approaching its final fund while still actively investing. The conversation explores why so many peopl…
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How To Implement Profit Protection Protocols To Stop Profit Leaks
14:26
14:26
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14:26Revenue doesn’t equal profit and without the right systems, your money can vanish before you see it. In this episode, I reveal how to implement the Profit Protection Protocol to stop leaks, safeguard margins, and take control of your cash flow. If you want predictable profit and financial confidence, this episode is a must-watch. 👇🏾 TAKE THE SAY YE…
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Pioneering Small Business Software & Empowering Entrepreneurs w/ Gail Goodman, Founder & CEO of Constant Contact
58:58
58:58
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58:58In this episode of Outsider Inc., host Ian Hathaway interviews Gail Goodman, former CEO of Constant Contact. Goodman discusses her journey from her early entrepreneurial endeavors to leading Constant Contact from startup to IPO and ultimately to a $1.1 billion acquisition. She emphasizes the importance of execution over ideas and how a deep commitm…
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What Happens When You Pay Yourself First and As The CEO
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14:07
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14:07Most CEOs pay everyone else first, the team, vendors, software, even taxes, while their own paycheck stays optional. This episode breaks down why that habit keeps you stuck in survival mode and how paying yourself first is a major sign of financial maturity and business growth. 👇🏾 TAKE THE SAY YES TO PROFITS QUIZ https://Quiz.SayYesToProfits.com 👇🏾…
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Starting and Closing a Bank in 3 Months with Bala Kamallakharan
49:08
49:08
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49:08In this episode of the Give First podcast, Brad Feld talks with Bala Kamallakharan, founder of Startup Iceland and a driving force behind the country’s modern startup ecosystem. Bala shares the remarkable story of moving to Mumbai to build an Icelandic bank in 2008, only to watch the entire financial system collapse overnight. Within three months, …
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Why More Revenue Doesn't Equal More Cash Flow or Profit
13:47
13:47
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13:47Growing revenue should create financial freedom… but for many CEOs, it creates chaos instead. In this episode, Dr. Octavia Conner reveals why business owners with impressive revenue often struggle with unpredictable cash flow, rising expenses, and constant financial uncertainty. You’ll learn the 3 core reasons cash disappears, even during growth, a…
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The 7 Deadly Financial Sins Service Based CEOs Make
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19:12Success has a dark side. Most established consulting firm owners and service-based CEOs don’t fail because of the economy, the market, or even competition. Nope. Many struggle or even fail because of their own shortcomings, which is the dark side of success. What am I referring to when I say you, yes, YOU, may be the dark side of success or the dow…
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Leading with Love, Staying Mission Focused, and Building a Multi-Billion-Dollar Business in Atlanta w/ Kyle Porter, Founder & fmr CEO of Salesloft
58:22
58:22
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58:22In this episode of Outsider Inc., host Ian Hathaway interviews Kyle Porter, founder and longtime CEO of SalesLoft. Kyle shares his remarkable journey from nearly failing in the first year of SalesLoft to scaling the company to unicorn status with a $2.3 billion valuation. He discusses the core principles of leadership, such as leading with love, st…
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How Pledge 1% Sparked a Global Movement for Startup Philanthropy
22:35
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22:35In this special episode of the Give First podcast, Brad Feld and Sameer Dholakia revisit the origins of Pledge 1%, the global movement helping startups build philanthropy into their business from the start. What began as a simple conversation in Boulder between Brad and Rally Software co-founder Ryan Martens grew into a worldwide initiative champio…
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From Introvert to IPO: Culture, Control, and Building SendGrid into a Category Leader w/ Isaac Saldana, Co-Founder & fmr CEO, SendGrid
53:52
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53:52In this episode of Outsider Inc., host Ian Hathaway interviews Isaac Saldana, the co-founder and former CEO of SendGrid, and current CEO of Joy Labs. Isaac discusses the interplay of humility and confidence in leadership and shares his unconventional path to success. From being a non-English-speaking teenager who managed a family and two jobs at 19…
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How Sameer Dholakia Led SendGrid to IPO and Exit
38:08
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38:08In this episode of the Give First podcast, Brad Feld sits down with Sameer Dholakia, partner at Bessemer Venture Partners and former CEO of SendGrid, the first Techstars company to go public. When Sameer joined SendGrid, growth was slowing and the company was losing money. Under his leadership, it became a $250M business, went public, and was later…
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The Compass Within: Robert Glazer on Leading with Core Values
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29:00In this episode of the Give First podcast, Brad Feld sits down with Robert Glazer, 5x entrepreneur, #1 Wall Street Journal and USA Today bestselling author, and author of the new book The Compass Within. Robert shares his framework for uncovering personal core values, the principles that guide decisions, relationships, and leadership. The conversat…
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From Midwest Outsider to Movement-Leading Industrialist: Choosing the Uphill Challenges and Rebuilding American Manufacturing w/ Aaron Slodov, Remesh & Atomic Industries
46:49
46:49
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46:49In this episode of Outsider Inc., our guest is Aaron Slodov, co-founder of Remesh and co-founder and CEO of Atomic Industries. Aaron shares insights from his unique journey from a child tinkering in Cleveland to working at Google X, and founding a series of innovative companies. The discussion delves into the challenges and opportunities in America…
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What Women CEOs Should Do During a Government Shutdown
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15:49
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15:49When the government shuts down, most women CEOs panic. But the prepared ones? They profit and thrive. In this episode of the Say Yes To Profits® Podcast, Dr. Octavia Conner reveals how to thrive, not fear, during a government shutdown. Discover two powerful strategies to protect your business, strengthen your network, and create independent revenue…
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How to Boost Profits Without Working More
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15:55
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15:55Ever had a client who paid well but left you exhausted and broke? Not all revenue is created equal, and let me show you why. In this episode, Dr. Octavia Conner shares the Revenue Quality Index (RQI), a simple yet powerful tool that shows you which revenue streams bring profit, peace, and scalability. Tune in and learn how to work less, earn more, …
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From Ironman Collapse to Healthcare Category Leader: Burning the Ships w/ Guillaume de Zwirek, Founder & CEO, Artera
58:00
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58:00In this episode of Outsider Inc., host Ian Hathaway interviews Guillaume de Zwirek, founder and CEO of Artera. Guillaume's journey from a classical guitarist and world-class Ironman triathlete to a successful health tech entrepreneur is anything but conventional. Inspired by his personal frustrations as a healthcare patient, Gui founded Artera, a p…
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You didn’t start your business to stress about money. Yet so many CEOs feel profitable but still run out of cash. In this episode of the Say Yes To Profits® Podcast, Dr. Octavia Conner simplifies cash flow so you can finally see where your money is going, stop financial chaos, and take control of your business growth. Inside this quick lesson, you’…
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AI First Leaders | Andy Sack & Adam Brotman on Scaling with the AI Wave
24:36
24:36
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24:36In this episode of the Give First podcast, David Cohen sits down with longtime Techstars friend Andy Sack and former Starbucks Chief Digital Officer Adam Brotman, co-CEOs of Forum3 and co-authors of AI First: The Playbook for a Future-Proof Business and Brand. They explore why AI isn’t just another vertical, but the foundation of how companies will…
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What Is a Virtual CFO and Why Your Business Can't Scale Without One
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13:18
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13:18What is a Virtual CFO, and why does your business need one? In this episode of the Say Yes To Profits® Podcast, Dr. Octavia Conner explains how a Virtual CFO goes beyond bookkeeping and accounting to design the financial strategy that drives long-term success. You will learn how a CFO creates clarity in your numbers, builds a cash flow system that …
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Capital-Constrained & Mission-Obsessed: How Pressure Forged a Healthcare Unicorn in Iowa w/ Jon Lensing, Co-Founder & CEO, OpenLoop
50:53
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50:53In this episode of Outsider Inc., host Ian Hathaway speaks with Jon Lensing, co-founder and CEO of OpenLoop, a telehealth infrastructure platform headquartered in Des Moines, Iowa. From growing up in rural Iowa to training as a surgeon, Jon's path took an unconventional turn when he left medicine to build a company addressing healthcare access. Sin…
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Building Startups and Lasting Relationships with Scott Dorsey
31:50
31:50
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31:50In this episode of the Give First podcast, Brad Feld talks with Scott Dorsey, co-founder of High Alpha and former CEO of ExactTarget, the email marketing pioneer acquired by Salesforce. Scott shares his journey from launching a startup with no technical background to building a company of 2,000 employees, going public, and running Salesforce Market…
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Founder, Operator, Investor: Lessons Across Every Seat in Latin American Tech w/ Jimena Pardo, Co-Founder, Carrot; Co-Founder & Managing Partner, Hi Ventures
53:33
53:33
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53:33In this episode of Outsider Inc., host Ian Hathaway speaks with Jimena Pardo, co-founder of Carrot, Mexico's first car-sharing platform, and now Co-Founder & Managing Partner at Hi Ventures. Jimena opens up about the rollercoaster of building Carrot, the lessons of operating in a tough market, and how she transitioned from founder to investor. She …
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How To Scale Your Business (so it operates without you)
19:25
19:25
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19:25Many CEOs dream of freedom, the ability to travel, take time off, and lead their business instead of managing every detail. But too often, they become the bottleneck. Every email, invoice, and client decision flows through them, leading to exhaustion, stalled growth, and team confusion. In this week’s episode, I share how real scalability begins wi…
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Breaking Barriers for Entrepreneurs with Elizabeth Gore
28:40
28:40
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28:40In this episode of the Give First podcast, Brad Feld talks with Elizabeth Gore, co-founder and president of Hello Alice, about what it takes to build and scale a platform serving over 1.5M small business owners. Elizabeth shares how Hello Alice became a critical lifeline during COVID, launching grant programs, pivoting product builds, and creating …
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Betting on Yourself, Breaking Into Tech, & Refusing to Take No for an Answer w/ Melodie van der Baan, Co-Founder & CEO, Max Retail
52:12
52:12
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52:12In this episode of Outsider Inc., host Ian Hathaway chats with Melodie van der Baan, co-founder and CEO of Max Retail. Melodie shares her unconventional journey from skipping college to diving into real estate, losing everything in the housing crash, and then transforming into a mobile designer clothes distributor. Her challenges and experiences ev…
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$89,000 Recovered By One CEO & CFO: A Cash Flow Win Story
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15:07For over three months, a 7-figure CEO waited on nearly $90,000 owed to her company, tightening cash flow, delaying growth, and draining reserves. Say Yes To Profits stepped in as her Virtual CFO, recovered $89,279.13, and secured systems to prevent future delays. These strategies not only recovered lost revenue but restored peace of mind and positi…
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Building Ecosystems from the Ground Up with Landon Young
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25:21In this episode of the Give First podcast, Brad Feld reconnects with Landon Young, pre-seed investor at Elevate Ventures and a longtime builder of startup ecosystems. Landon shares stories from both sides of the table, as a founder and investor, including what it means to write the first check when a company is still just a sketch on a napkin. They…
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Is your business financially successful, or just surviving on revenue alone? This episode of the Say Yes To Profits Podcast challenges CEOs to move beyond avoidance or surface-level analysis. It’s a call to take ownership of your financial narrative now, while you still have the power to shape the outcome, rather than later, when the cost of inacti…
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From Visual Search Founder to Visionary VC w/ Jewel Burks Solomon, Co-Founder of Partpic & Managing Partner, Collab Capital
52:54
52:54
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52:54In this episode of Outsider Inc., host Ian Hathaway interviews Jewel Burke Solomon, a founder, investor, and community leader based in Atlanta. Jewel shares her experiences of co-founding PartPic, a startup designed to identify and replace industrial parts through visual search technology, which was later acquired by Amazon. She discusses her chall…
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How to Stop Feeling Broke in Your 7-Figure Business
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23:19
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23:19You can generate $1 million in revenue and still feel broke. Why? Because revenue is not cash. In this episode of the Say Yes To Profits Podcast, I will break down the real reasons high-earning CEOs are financially stressed and what to do about it. From delayed receivables to bloated expenses and the “spend to grow” trap, you’ll uncover the profit-…
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How Policy Shapes Startups: Bobby Franklin on the VC Industry’s Silent Battle
32:23
32:23
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32:23In this episode of the Give First podcast, Brad Feld sits down with Bobby Franklin, President and CEO of the National Venture Capital Association (NVCA). They unpack the disconnect between Washington, D.C., and the startup world, and why that gap poses a growing threat to innovation in the U.S. Bobby shares stories from the front lines of venture p…
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A Bookkeeper and CPA Are No Longer Enough For 7-Figure CEOs.
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15:02You are running a 7-figure-plus business. You have a CPA and a bookkeeper. So why do your finances still feel unclear and disconnected? The truth is, this is not a revenue issue. It is a financial leadership gap. In this episode of the Say Yes To Profits Podcast, I explain why a Virtual CFO is the missing piece and how to finally gain financial cla…
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Founder, Filmmaker, Humanitarian, & VC: Reinvention through Purpose w/ Sean O'Sullivan, Co-Founder of MapInfo & Managing GP, SOSV
51:21
51:21
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51:21This episode of Outsider Inc. features Sean O'Sullivan, Co-Founder of MapInfo & Managing General Partner of SOSV. Host Ian Hathaway leads the conversation with the digital mapping pioneer, deep tech investor, and humanitarian, as he shares his extraordinary journey from co-founding MapInfo, a revolutionary digital street mapping system, to his role…
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The Near Death (and Rebirth) of Simple Energy with Justin Segall & Yoav Lurie
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41:13In this episode of the Give First podcast, Brad Feld sits down with longtime friends and Simple Energy co-founders, Justin Segall and Yoav Lurie. Together, they revisit a pivotal moment in their startup journey, when the company was on the verge of collapse. The conversation dives into the chapter inspired by their experience in Brad’s new book, Gi…
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12 Financial Commandments for 7-Figure Women CEOs
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23:47
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23:47Generating millions in revenue does not guarantee consistent profit, cash flow clarity, or financial stability. In this episode of the Say Yes To Profits® Podcast, Dr. Octavia Conner, Virtual CFO and Business Financial Strategist for 7-figure service-based women CEOs, reveals the 12 non-negotiable financial commandments that every high-earning CEO …
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Givers, Takers, and Building Cultures That Last with Adam Grant
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38:23In this episode of the Give First podcast, Brad Feld sits down with organizational psychologist and bestselling author, Adam Grant, for a conversation about the power of generosity in business, leadership, and life. Brad and Adam trace the roots of give first and give and take, uncovering how their philosophies arrived at the same conclusion: that …
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4 Underrated Cash Flow Strategies for Scaling CEOs
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20:52Most 7-figure CEOs believe that increasing revenue solves cash flow problems. It does not. In this episode, Dr. Octavia Conner reveals five strategic cash flow systems that high-earning CEOs must implement to eliminate gaps, protect profit, and lead with financial control. You will learn: Why your business may look profitable but still feel financi…
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