loader from loading.io

How I Raised My Seed, Series A, & Series B

Ambition Today, Startup Stories with Kevin Siskar

Release Date: 10/29/2024

How I Raised My Seed, Series A, & Series B show art How I Raised My Seed, Series A, & Series B

Ambition Today, Startup Stories with Kevin Siskar

This episode of Ambition Today is supported by:  In October 2024, Finta hosted a panel for LA Tech Week called “How I Raised - Seed, Series A, Series B.” Featuring founders exploringthe unique challenges and insights of securing capital at different stages of their company. Our incredible panel for this event consists of: David Kervin‍ Proteus Space ($8M Raised) - Revolutionizing satellite design with AI-driven platforms, aiming to reduce the time and cost of deploying satellites through automation and cutting-edge technology. Gaurav Bhattacharya Jeeva ($16M Raised) -...

info_outline
Fundraising Perspectives From 3 Sides Of The Table: An Investor, a Founder, and a Lawyer show art Fundraising Perspectives From 3 Sides Of The Table: An Investor, a Founder, and a Lawyer

Ambition Today, Startup Stories with Kevin Siskar

During NY Tech Week 2024 we hosted a live panel discussion in midtown Manhattan on the state of fundraising in 2024. Delving deep into the nuances of fundraising from three different perspectives: an investor, a founder, and a lawyer. Hear from 3 different sides of the table when we gather an investor, founder, and a lawyer to discuss what fundraising venture capital in 2024. Our incredible panel for this event consists of: ​The Founder ‍David Silverstein, is the CEO of Ned, a white label lending platform that makes it easy for lenders to effortlessly deploy capital. The Investor Rachel...

info_outline
How Lorenzo Thione Is Scaling Support For Diverse Founders With Gaingels show art How Lorenzo Thione Is Scaling Support For Diverse Founders With Gaingels

Ambition Today, Startup Stories with Kevin Siskar

We sat down with one of the most influential people in tech, Lorenzo Thione, who shares his very inspiring journey and how that led him to be where he is today. Lorenzo grew up in Milan, Italy and had a technical background at an early age. He completed his studies at the University of Texas at Austin, from which he holds a M.S. in Computer Engineering. He is now the Managing Director of Gaingels, a leading LGBTQIA+/Allies investment syndicate and one of the largest and most active private investors in North America. He is also the co-founding Chairman of StartOut, Chairman of the Board at...

info_outline
How Jordan Levy Left His Mark On The Venture Capital Industry show art How Jordan Levy Left His Mark On The Venture Capital Industry

Ambition Today, Startup Stories with Kevin Siskar

In the fall we sat down with one of the godfathers of Venture Capital, Jordan Levy, who shares his very inspiring founder story and how that led to his career as an investor. Jordan co-founded Software Distribution Services which was acquired by Ingram Micro, before going on to be a Partner on the early-stage investing team at SoftBank Capital (SBNY) for 16 years. Jordan has served on the boards of BuzzFeed, TalkSpace, , ACV Auctions, and many others. Using his upbringing and religion to pay it forward (Tzedakah) to the community that he grew up in, in Buffalo, New York. Jordy also...

info_outline
Scott Wayman's Plan for Kangarootime to Support the $648 Billion Care Economy show art Scott Wayman's Plan for Kangarootime to Support the $648 Billion Care Economy

Ambition Today, Startup Stories with Kevin Siskar

Scott Wayman's shares his epically inspiring founder story. His passion for Kangarootime is next level and the company is currently focused on winning the childcare management software space for daycares and preschools. With plans to expand to the larger “care economy” which includes not only early education & childcare but also elder & senior care. A $648B TAM in the U.S. Alone according to . The Kangarootime team brilliantly positioned themselves throughout COVID19 as leaders in the space, by taking time to host educational sessions about how their customers can best adapt...

info_outline
Creating Data-Driven Sales Leaders With Peter Kazanjy show art Creating Data-Driven Sales Leaders With Peter Kazanjy

Ambition Today, Startup Stories with Kevin Siskar

Pete Kazanjy is Ambition Today’s new guest from Southern California. He is sitting in San Francisco, CA right now as we speak, enjoying Alamo Square. He is a serial founder and seasoned early stage Saas executive, advisor, and investor. Pete has cofounded many companies including TalentBin, Modern Sales, and Atrium. He is also an author of “Founding Sales”. He went to Stanford where he learned English and Philosophy. Pete is still going strong and has a lot to offer his clients, be sure to read his book “Founding Sales”, a Startup Sales Handbook. Topics Discussed: Branding and...

info_outline
Jack Greco Builds A Unicorn Company In Buffalo show art Jack Greco Builds A Unicorn Company In Buffalo

Ambition Today, Startup Stories with Kevin Siskar

  From growing up on a dairy farm, to a successful entrepreneur with hundreds of employees, meet our next guest, Jack Greco. Greco co-founded ACV Auctions, an online auction dealer platform, which was last valued at $1.5B. He never thought that he would be the person to co-found Buffalo’s first unicorn startup in 2014. The great part is the story behind his success. He later reveals to Kevin that he has been fired from every job before he became a founder, and what kicked him in gear, was learning that he had a baby on the way. Every success story is different, and I think...

info_outline
News Roundtable: Future of American Cities and Working From Home show art News Roundtable: Future of American Cities and Working From Home

Ambition Today, Startup Stories with Kevin Siskar

  Kevin Siskar and Tim Shisler are at it again, discussing the current news in our world today. Each person brings one topic to the table and they talk about them both. Kevin’s Topic: The Future of American Cities. Kevin starts by discussing how he lived in NYC for a full decade and how he has seen the cost of living has increased significantly, but at the same time, the storefronts are leaving! This is due to the commercial investors also increasing their rent too much where small shops are no longer able to handle the cost. Kevin found a statistic: 50% of all restaurants in...

info_outline
Bringing Back Jeff Wald To Discuss The End Of Jobs show art Bringing Back Jeff Wald To Discuss The End Of Jobs

Ambition Today, Startup Stories with Kevin Siskar

Our next guest is so amazing, we had to interview him a second time! He was on nearly 5 years ago on Episode 8! Jeff Wald is an entrepreneur who has started three technology companies, with his latest company, WorkMarket, being sold to ADP. Monday was officially his last day. He is a Board Member on the following boards: Steel Connect, Costar Technologies, TransfrVR, Peerless Systems, and Register.com. But the true reason we brought him on the podcast today was to talk about his book, “The Rise of On-Demand Workers and Agile Corporations”. Tune in to hear all about his book as well as...

info_outline
News Roundtable: R.I.P. to RBG and Facebook show art News Roundtable: R.I.P. to RBG and Facebook

Ambition Today, Startup Stories with Kevin Siskar

In this new episode, Kevin Siskar and Tim Shisler discuss the current news in our world today. Each week, each person brings one topic to the table. This week Tim chose to talk about the sad passing of former Associate Judge, Ruth Bader Ginsburg on September 18, 2020. She passed away after complications of metastatic pancreatic cancer. And brought Facebook to the table. There are real issues with Facebook. Everything from the false advertising that Facebook is not taking responsibility for, mental health issues stemming from addiction to Facebook, and now election interference! On...

info_outline
 
More Episodes

This episode of Ambition Today is supported by: Finta, The Capital Copilot 

In October 2024, Finta hosted a panel for LA Tech Week called “How I Raised - Seed, Series A, Series B.” Featuring founders exploringthe unique challenges and insights of securing capital at different stages of their company. Our incredible panel for this event consists of:

David Kervin

Proteus Space ($8M Raised) - Revolutionizing satellite design with AI-driven platforms, aiming to reduce the time and cost of deploying satellites through automation and cutting-edge technology.

Gaurav Bhattacharya

Jeeva ($16M Raised) - Harness AI-driven customer intelligence, helping companies optimize their customer experience and reduce churn through actionable insights​.

Scott Wayman

Kangarootime ($37.5M Raised) - A leading innovator in the childcare management software industry, Kangarootime has risen to the forefront, providing vital solutions for daycares and preschools.

 

Key Fundraising Insights From This Episode:

1. Getting Investor Buy-In: Confidence Over Convincing

Founders emphasized that successful fundraising begins with confidence, not just pitching facts. Believing in your mission sets the tone for investor meetings, as confidence drives a stronger, more resonant narrative.

2. Parallel vs. Sequential Fundraising Processes

Gaurav shared that sequential meetings can be a trap, leading to prolonged efforts. Instead, structuring outreach as a concentrated, parallel push creates urgency and FOMO among investors, leading to quicker commitments.

3. Navigating Round Dynamics with Clear Milestones

For each funding stage, specific milestones are critical. Scott noted that Series B investors expect well-established product-market fit and sales efficiency, while Series A focuses on validating product intent. Seed rounds, by contrast, require strong founder conviction and a scrappy dedication.

4. Leveraging Warm Intros for Better Outcomes

Cold outreach has a low conversion rate. David and Gaurav underscored the importance of warm intros, building relationships long before “the ask,” as connections formed early often convert to funding opportunities.

5. Pitfalls in Equity Structure and Term Negotiations

Gaurav and Scott highlighted the importance of a clean cap table and an informed approach to term sheets, particularly for liquidation preferences and convertible notes, which can heavily dilute founder control if unchecked.

6. Evolving Pitch Focus: Metrics Over Mission at Later Stages

With each funding stage, the pitch shifts. For Series B, Scott mentioned that metrics and market dynamics become critical to justify high-value funding rounds, moving beyond storytelling toward quantifiable business growth.

7. The Role of Timing and Market Trends

Market trends, such as the rise of AI, can be powerful, but founders caution to present technology realistically. David shared that aligning milestones with tech waves and managing investor perceptions is essential for positioning within emerging sectors.

8. Finding the Balance in Deal Terms and Equity Retention

David noted that while SAFE notes and convertible debt can expedite early funding, they can also lead to significant dilution. Founders should prioritize understanding term sheets and use cap table modeling tools like Carta to project long-term equity impacts.

9. Building and Utilizing Investor Relationships Over Time

David emphasized the value of maintaining relationships with VCs who may not invest immediately. Regular updates and casual interactions allow investors to track your progress and feel more comfortable when it’s time to commit.

10. Strategic Use of Milestones to Drive Up Valuation

Meeting critical operational or revenue milestones before the next round can significantly enhance valuation and interest. Scott’s journey highlighted that proving product-market fit and high sales efficiency before Series B can allow for strong, valuation-focused negotiations.

11. Positioning Within Tech Waves for Strategic Advantage

Each wave of technology (e.g., AI, blockchain) offers a unique angle for storytelling and market positioning. Scott and Gaurav recommended founders lean into tech trends authentically, showcasing how the wave aligns with their product rather than simply following hype.

Hosting this event was a blast! A massive thank you to everyone who helped make this event happen and a success. We can't wait to see you all at the next one!

 

 

 

==========
Visit Ambition Today on the Web: ​www.siskar.co/ambitiontoday
Follow Kevin Siskar on Twitter: ​twitter.com/TheSiskar
Follow Kevin Siskar on Instagram: instagram.com/thesiskar
Follow Kevin Siskar on Facebook: facebook.com/kevin.siskar
Add Kevin Siskar on Snapchat: snapchat.com/add/krsiskar

Kevin Siskar brings you ambitious entrepreneurs inspired by Tim Ferriss Show, How I Built This with Guy Raz, Residual Income, Entrepreneur on Fire, NPR, HBR, TED Radio Hour, the StartUp podcast with Alex Blumberg by Gimlet Media, Pat Flynn, Tony Robbins, The Uncertain Hour, Bigger Pockets, Art of Charm, Dave Ramsey, Planet Money, Jocko Podcast, EntreLeadership, Zigler, APM Marketplace, This Week In Startups with Jason Calacanis, Mixergy, Seth Godin, Joe Rogan Experience, GaryVee, James Altucher, Monocle 24, How to Start a Startup, Crooked Media, and The $100 MBA Show with Omar Zenhom, and Casey Neistat.

Be sure to listen and subscribe to Ambition Today in the iTunes Store for iOS (apple.co/1NRRPzL), on Google Play Music (goo.gl/LmmciJ), or on Stitcher for Android (bit.ly/1Rn01dy).