loader from loading.io

How to Think Strategically about Funding for Founders and Investors

The Conversation Factory

Release Date: 05/09/2023

Leading with Respect with Marcy Syms show art Leading with Respect with Marcy Syms

The Conversation Factory

Marcy Syms is a pioneering businesswoman and advocate for respect in leadership. She’s seen leadership fads come and go. She was a CEO when people still thought “women shouldn’t do that sort of thing”  And she’s done something many folks have never had to endure - shuttering her family’s business while making her key creditors whole - an act deeply in line with her core value of respect. Marcy shares insights from her journey in the retail industry, her experiences with leadership dynamics  and her advocacy for the Equal Rights Amendment - something she hopes to see made...

info_outline
The Seven Everyday Habits for Transforming Systems show art The Seven Everyday Habits for Transforming Systems

The Conversation Factory

Download free chapters from : Listen now 👇 🎙️ Spotify: 🍎 Apple:   And please  or Also! support the podcast with  or a : Full show notes:    SUMMARY In this conversation, Adam Kahane discusses the complexities of transforming systems, emphasizing the importance of understanding systems thinking, collaboration, and the role of individual contributions. He shares insights from urban transformation examples, the significance of culture, and the necessity of engaging with systems responsibly. Kahane introduces seven habits for transforming systems,...

info_outline
Innovation, Connection, and Conscious Leadership with Othership CEO Robbie Bent show art Innovation, Connection, and Conscious Leadership with Othership CEO Robbie Bent

The Conversation Factory

Get free chapters of my book, Good Talk, and master the art of conversations big and small: https://www.danielstillman.com/good-talk Please support the podcast! 💌 : https://spoti.fi/3QzcPAW 💌 : or with : https://bit.ly/support-tcf-monthly : https://bit.ly/support-tcf-once Check out for the full transcript and video highlights. Episode page: https://theconversationfactory.com/podcast/innovation-connection-and-conscious-leadership-with-othership-ceo-robbie-bent AI Summary: Introduction and Connection: Daniel Stillman introduces Robbie Bent, highlighting the connection through mutual...

info_outline
The Founder's Financial Compass: Navigating Emotions and Assumptions with Fractional CFO Lauren Pearl show art The Founder's Financial Compass: Navigating Emotions and Assumptions with Fractional CFO Lauren Pearl

The Conversation Factory

Get free chapters of my book, Good Talk, and master the art of conversations big and small: Please support the podcast! 💌 : 💌 : or with : : Check out  for the full transcript and video highlights. Money! It can be an emotional topic. But, as my guest on today's podcast, fractional CFO Lauren Pearl says, it's emotional for everyone in different ways! In this episode, Lauren reveals her perspectives on how to approach these difficult conversations. Given how many leaders she’s worked with, we also explore her thinking about effective leadership, intentional...

info_outline
Join or Die: Behind the Scenes of Creative Collaboration show art Join or Die: Behind the Scenes of Creative Collaboration

The Conversation Factory

Get free chapters of my book, Good Talk, and master the art of conversations big and small: Please support the podcast! 💌 : https://spoti.fi/3QzcPAW 💌 : or with : https://bit.ly/support-tcf-monthly : Check out for the full transcript and video highlights: Key Chapters 00:00 Growing Up Together: A Family Legacy 02:58 The Birth of a Documentary Idea 06:02 Navigating the Journey: Challenges and Growth 09:02 The Lens of Community: A New Perspective 12:01 Conflict and Collaboration: The Art of Working Together 14:54 The Long Haul: Commitment and Transformation 22:15 The Transformative...

info_outline
Founder-Led Sales and Building Co-founder Relationships show art Founder-Led Sales and Building Co-founder Relationships

The Conversation Factory

Get free chapters of my book, Good Talk, and master the art of conversations big and small: Please support the podcast! 💌 : https://spoti.fi/3QzcPAW 💌 : or with : : Check out for the full transcript and video highlights. We break down:  The Importance of Deep and Authentic Conversations and unpack how Natalise fosters honest and open conversations and has worked to build a company culture that reflects these values.  Intentional Co-founder Relationship Building: We talk about how Natalise and her co-founder, Nathan Brown, approached building a strong relationship...

info_outline
The Inner Work of Leadership with Carole Robin, PhD show art The Inner Work of Leadership with Carole Robin, PhD

The Conversation Factory

Master the art of conversations big and small - both inside yourself and in your teams and organization. Get free chapters of my book, Good Talk: Please support the podcast! 💌 Subscribe on Spotify: 💌 iTunes: or with a monthly contribution here: or make a one-time donation here:  For the full transcript, video highlights, and more show links, check out the episode page here: Every conversation - especially the hard ones - is an opportunity to learn more about yourself, to learn about another person and to learn about interpersonal dynamics - if you can set aside judgment...

info_outline
Your Brain on Beautiful Conversations with Anjan Chatterjee show art Your Brain on Beautiful Conversations with Anjan Chatterjee

The Conversation Factory

Download free chapters from Please support the podcast by  or , making , or making . Check out for the full transcript and video highlights. Dr. Anjan Chatterjee is a renowned professor and the founding Director of the Penn Center for Neuroaesthetics. He's a leading expert on how our brains perceive beauty and art, and author of an engaging book on this topic: “The Aesthetic Brain: How We Evolved to Desire Beauty and Enjoy Art" In this beautiful conversation, we explore: the intersection of beauty, conversation, and the human brain how our biological evolution has...

info_outline
Changing the Political Conversation with Nick Troiano show art Changing the Political Conversation with Nick Troiano

The Conversation Factory

If you want to change the game, changing the rules and incentives of the game is a powerful approach. Few people who watch the news - or those folks who avoid watching the news! - would say the political system in the United States is going according to plan. The founding fathers, if they were alive today, would be aghast at the unbridgeable chasm that seems to have developed in our political culture, making dialogue, compromise and progress nearly impossible on some of our most pressing issues.  In fact, our founding fathers warned against the rise of what they called factions in their...

info_outline
The Secrets of Motivation and Systems Change with Becca Block, PhD show art The Secrets of Motivation and Systems Change with Becca Block, PhD

The Conversation Factory

Warning - this episode uses a specific curse word - a lot. And once we started using one, we started using more of them. So…if f-bombs, sprinkled like salt are not your cup of tea, this is a good episode to skip! My guest today is Rebecca R Block, PhD, who is an expert in helping organizations build programs, services and products that equip young people to develop the confidence and skills they need to enter adulthood as thriving and adaptable lifelong learners. She has spent the last 14 years leading the design, improvement, and evaluation of educational programs and services to make them...

info_outline
 
More Episodes

I first met Avantika Daing, a General Partner & Managing Partner at Plum Alley Investments (and Tedx Speaker!) while she was onstage at an Entrepreneurs Roundtable Accelerator event. She was there to share a bit about Plum Alley’s Investment thesis as well as unpack six pitches live from early-stage companies.

Let’s level set a bit so you understand Avantika’s and Plum Alley’s mission, which revolves around an important number that hasn’t moved much in years, despite a lot of effort - 2%. 

According to Pitchbook, in 2022, companies founded solely by women garnered just 2% of the total capital invested in VC-backed startups in the United States. Plum Alley only funds gender-diverse companies and works to create an ecosystem to help them not just get funded, but to grow and succeed. That’s one of the reasons I wanted to bring Avantika on, to share some of her ways of thinking strategically about funding as an investor, how Plum Alley is working to create a more sustainable funding ecosystem for diverse founding teams, and how she coaches founders to be more strategic about funding, too.

Watching Avantika on stage peel back the layers of the onion (one of her favorite metaphors!) on a company’s story in conversation with a founder and work to understand the company’s potential was fascinating - it’s a tremendous act of intellectual rigor and curiosity. Her questions also reminded me that founders can make an investor’s job a lot easier through more powerful and intentional storytelling.

Another powerful metaphor that Avantika came back to in a number of pitches was the idea of a Basecamp.

In other words, Avantika, as a funder, wants to know: Is your company building a core technology or defensible market position (a basecamp) that will provide you with multiple paths to success? 

Avantika acknowledged that a “single story” about how your company will “win” or “summit the mountain” is powerful, but she was clear that she prefers companies that are creating a powerful “basecamp”...why? Because:

🏒A “many shots on goal” strategy can help create longevity and increase options for success.

I’m so grateful that she was willing to have a longer conversation with me on the record to explain her ideals about storytelling and the basecamp-summit metaphor.

She also helped peel back some layers on another idea she loves to coach founders on: “Dressing their cap table” for sustainable success from seed to IPO and well beyond - since capital needs don’t stop at IPO.

I love how Avantika’s metaphors shift,  refocus and redesign the conversation about pitching, funding and sustainable success for startups.

Enjoy this conversation as much as I did!

Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders.

Links

Plum Alley

Avantika's Tedx Talk: There is No Balance. There is Juggling

Daniel’s LI post on Avantika’s Entrepreur’s Roundtable Session, highlighting key questions and perspectives from Avantika, including the “base camp/summit” metaphor.