Jaclyn Johnson is a powerhouse entrepreneur, investor, and advocate for women in business.By 35, she had already launched and sold two multimillion-dollar companies, including Create & Cultivate, a first-of-its-kind platform for female entrepreneurs that scaled to eight-figure revenue and partnered with Fortune 500 brands like Amazon, Mastercard, and Microsoft.Now, she’s back with Cherub, a double-sided marketplace designed to bridge the gap between underrepresented founders and democratizing access to category-defining companies. As both an angel investor and advisor, Jaclyn has backed businesses like Away, Live Tinted, and Chillhouse, bringing hard-won experience from her own journey into the founder–funding relationship.Subscribe nowIn this conversation, we break down:Jaclyn’s origin story: why she built CherubHow she approaches angel investing and the lessons she’s learnedWhat makes a great angel pitch (and what doesn’t)The realities of being an accredited investorWhy representation in funding isn’t just moral, it’s market-changingChapters00:00 The Importance of Angel Investments02:49 Jaclyn’s Journey as a Founder and Investor05:41 Understanding Angel Investors vs. Venture Capitalists08:28 The Role of Angel Advisors11:23 Building Relationships with Angels14:15 The Power of Brand Fame17:25 Cherub’s Mission and Deal Flow20:07 Educating Angels and Standardizing Investments23:13 Creating Effective Fundraising Pages26:12 The Role of Analytics in Fundraising29:04 Onboarding Founders to Cherub32:01 Connecting with Angels: Best Practices35:03 Diversifying the Investment Landscape37:58 The Future of Angel Investing40:35 Special Offers for Founders on CherubGuest BioJaclyn Johnson is the founder of Cherub and creator of Create & Cultivate, which she scaled to an eight-figure exit while reshaping how brands and communities support female entrepreneurs. Named a Forbes 30 Under 30 and an Adweek Disruptor, Jaclyn is an angel investor and advisor to companies including Away, Live Tinted, and Chillhouse. She’s dedicated to making capital and community more accessible for underrepresented founders while equipping the next generation of women entrepreneurs to scale.Who Should ListenFounders raising their first angel roundEntrepreneurs seeking representation and resourcesPeople curious about Angel Investing and how to get startedOperators looking to understand the angel landscapeMusic Credit“Neptuno” – Phondupe (Album: Onykia)Access All Areas.Listen: Apple || Spotify || YouTubeSubscribe: SubstackCommunity & Events: Founders CircleConnect: LinkedInSocials: TikTok || Instagram || XWeb: startupsdecoded.com
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Jaclyn Johnson is a powerhouse entrepreneur, investor, and advocate for women in business.By 35, she had already launched and sold two multimillion-dollar companies, including Create & Cultivate, a first-of-its-kind platform for female entrepreneurs that scaled to eight-figure revenue and partnered with Fortune 500 brands like Amazon, Mastercard, and Microsoft.Now, she’s back with Cherub, a double-sided marketplace designed to bridge the gap between underrepresented founders and democratizing access to category-defining companies. As both an angel investor and advisor, Jaclyn has backed businesses like Away, Live Tinted, and Chillhouse, bringing hard-won experience from her own journey into the founder–funding relationship.Subscribe nowIn this conversation, we break down:Jaclyn’s origin story: why she built CherubHow she approaches angel investing and the lessons she’s learnedWhat makes a great angel pitch (and what doesn’t)The realities of being an accredited investorWhy representation in funding isn’t just moral, it’s market-changingChapters00:00 The Importance of Angel Investments02:49 Jaclyn’s Journey as a Founder and Investor05:41 Understanding Angel Investors vs. Venture Capitalists08:28 The Role of Angel Advisors11:23 Building Relationships with Angels14:15 The Power of Brand Fame17:25 Cherub’s Mission and Deal Flow20:07 Educating Angels and Standardizing Investments23:13 Creating Effective Fundraising Pages26:12 The Role of Analytics in Fundraising29:04 Onboarding Founders to Cherub32:01 Connecting with Angels: Best Practices35:03 Diversifying the Investment Landscape37:58 The Future of Angel Investing40:35 Special Offers for Founders on CherubGuest BioJaclyn Johnson is the founder of Cherub and creator of Create & Cultivate, which she scaled to an eight-figure exit while reshaping how brands and communities support female entrepreneurs. Named a Forbes 30 Under 30 and an Adweek Disruptor, Jaclyn is an angel investor and advisor to companies including Away, Live Tinted, and Chillhouse. She’s dedicated to making capital and community more accessible for underrepresented founders while equipping the next generation of women entrepreneurs to scale.Who Should ListenFounders raising their first angel roundEntrepreneurs seeking representation and resourcesPeople curious about Angel Investing and how to get startedOperators looking to understand the angel landscapeMusic Credit“Neptuno” – Phondupe (Album: Onykia)Access All Areas.Listen: Apple || Spotify || YouTubeSubscribe: SubstackCommunity & Events: Founders CircleConnect: LinkedInSocials: TikTok || Instagram || XWeb: startupsdecoded.com
S2E5: How AI Agents Ran Our Business, While I Went To Burning Man (with Adam Robinson)
Startups Decoded
45 minutes
3 weeks ago
S2E5: How AI Agents Ran Our Business, While I Went To Burning Man (with Adam Robinson)
OpenAI’s latest “Zapier-killer” headlines were sobering, but Adam Robinson already did the unthinkable: he removed every human from RB2B, a $6M ARR SaaS, for seven days and let AI agents run sales, support, and onboarding, zero intervention.The outcome?Revenue growth held (+4%/mo), 96.6% answer accuracy in sales chats, and 89% support resolution with no customer meltdowns.In this conversation, Adam unpacks:The real playbook behind the stuntWhy he designs his business to fit AI tools (not the other way around)How great documentation and Intercom Fin “guidance” drive resolution,Where agent workflows replace repetitive tickets,Why he’s doubling down on PLG, freemium, and simplicity, even in a high-churn category.We get into transparency, customer expectations, and why a profitable, small team can now beat over-tooled incumbents.Also: Yes, the week he “disappeared,” Adam was off-grid at Burning Man.Subscribe nowChapters00:00 Why agents now (and the OpenAI “Zapier-killer” moment)02:06 From Lehman Brothers to bootstrapped SaaS operator04:56 The 7-day no-humans experiment: scope & safeguards09:07 Build-to-AI: shaping product so agents can handle the work12:50 Lean, profitable, small: the appeal of a high-margin micro-org17:35 Adapting process to tools (not tools to process)23:06 Intercom Fin “guidance,” escalations, and transparency25:44 Churn reality: category dynamics and buyer persona30:10 Agent workflows: auto-diagnosing email invites (SendGrid)34:05 Feedback loops: weekly founder calls and customer insights39:19 Human connection vs. agent efficiency in 202542:33 Embracing imperfection—and why “simple wins”Guest BioAdam Robinson is Founder & CEO of Retention.com and RB2B. He bootstrapped Retention.com from $0 to $22M ARR in four years and previously built Robly to an eight-figure exit. A former CDS trader at Lehman Brothers/Barclays, he now builds lean, profitable SaaS—and publishes the receipts.Who Should ListenSaaS founders optimizing for profitability over headcountOperators implementing AI in sales, support, and onboardingInvestors tracking agentic automation and PLG at scaleBuilders designing “self-running” products and processesMusic Credit“Neptuno” – Phondupe (Album: Onykia)Access All Areas.Listen: Apple || Spotify || YouTubeSubscribe: SubstackCommunity & Events: Founders CircleConnect: LinkedInSocials: TikTok || Instagram || XWeb: startupsdecoded.comStartups Decoded is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.
Startups Decoded
Jaclyn Johnson is a powerhouse entrepreneur, investor, and advocate for women in business.By 35, she had already launched and sold two multimillion-dollar companies, including Create & Cultivate, a first-of-its-kind platform for female entrepreneurs that scaled to eight-figure revenue and partnered with Fortune 500 brands like Amazon, Mastercard, and Microsoft.Now, she’s back with Cherub, a double-sided marketplace designed to bridge the gap between underrepresented founders and democratizing access to category-defining companies. As both an angel investor and advisor, Jaclyn has backed businesses like Away, Live Tinted, and Chillhouse, bringing hard-won experience from her own journey into the founder–funding relationship.Subscribe nowIn this conversation, we break down:Jaclyn’s origin story: why she built CherubHow she approaches angel investing and the lessons she’s learnedWhat makes a great angel pitch (and what doesn’t)The realities of being an accredited investorWhy representation in funding isn’t just moral, it’s market-changingChapters00:00 The Importance of Angel Investments02:49 Jaclyn’s Journey as a Founder and Investor05:41 Understanding Angel Investors vs. Venture Capitalists08:28 The Role of Angel Advisors11:23 Building Relationships with Angels14:15 The Power of Brand Fame17:25 Cherub’s Mission and Deal Flow20:07 Educating Angels and Standardizing Investments23:13 Creating Effective Fundraising Pages26:12 The Role of Analytics in Fundraising29:04 Onboarding Founders to Cherub32:01 Connecting with Angels: Best Practices35:03 Diversifying the Investment Landscape37:58 The Future of Angel Investing40:35 Special Offers for Founders on CherubGuest BioJaclyn Johnson is the founder of Cherub and creator of Create & Cultivate, which she scaled to an eight-figure exit while reshaping how brands and communities support female entrepreneurs. Named a Forbes 30 Under 30 and an Adweek Disruptor, Jaclyn is an angel investor and advisor to companies including Away, Live Tinted, and Chillhouse. She’s dedicated to making capital and community more accessible for underrepresented founders while equipping the next generation of women entrepreneurs to scale.Who Should ListenFounders raising their first angel roundEntrepreneurs seeking representation and resourcesPeople curious about Angel Investing and how to get startedOperators looking to understand the angel landscapeMusic Credit“Neptuno” – Phondupe (Album: Onykia)Access All Areas.Listen: Apple || Spotify || YouTubeSubscribe: SubstackCommunity & Events: Founders CircleConnect: LinkedInSocials: TikTok || Instagram || XWeb: startupsdecoded.com
