In this episode of The Back Channel, we talk about the pressure founders feel to pitch a massive vision — and what actually makes that land with investors. VCs need to believe in billion-dollar outcomes, but that doesn’t mean you should throw out the biggest idea you can think of. Credibility, traction, and storytelling all shape how your vision is received. We also revisit the Airbnb pitch and why their big thinking worked — and how yours can too.

In this episode, we'll talk about green flags—the little things founders say or do that quietly leave a strong impression on investors. I share a story about a first-time founder at one of our events who said two things that really stood out. They weren’t flashy, but they revealed a surprising level of maturity... and they’re the kind of signals that stick.

In this episode of The Backchannel, we break down a simple but powerful equation to help founders understand why some investor meetings turn into momentum—and others fall flat. We share a personal story that sparked the idea, then introduce the concept of Time Given (TG) minus Time to Interest (TTI) as a way to diagnose and improve your fundraising outcomes. If you're stuck wondering why some pitches connect and others don’t, this framework might give you a clearer path forward.

Is pre-seed fundraising harder than ever? In this episode of The Backchannel, we break down how expectations for early-stage startups have shifted. Investors now demand more proof—traction, paying customers, and even product builds—before writing checks. Why? A mix of AI-driven productivity, global talent access, and the lingering effects of the post-ZIRP investment climate. If you’re a founder navigating this new reality, this episode will help you understand what it takes to stand out. Learn how to adapt, leverage AI tools, and make progress without investor capital. Tune in to stay ahead of the curve.

Setting deadlines in fundraising can be a powerful tool—or a costly mistake. In this episode of The BackChannel, we break down how founders should think about creating urgency without scaring off investors. Learn why setting deadlines too early can backfire, how to structure a process that keeps investors engaged, and why a well-placed deadline can actually help VCs prioritize your deal. If you're raising money and wondering how to create momentum without turning investors away, this one's for you.

Investors love to test founders with tough questions—but what if you don’t know the answer? In this episode, we break down a real pitch meeting where a simple misunderstanding derailed the conversation. Learn how to handle tricky investor questions, when to ask for clarification, and why truly knowing your business makes all the difference.

In this episode of the Back Channel, we explore the art of storytelling and the balance between hard facts and narrative. A founder’s question sparks a conversation about when to lean on data and when to let the story take center stage. Tune in for thought-provoking insights on crafting compelling narratives without getting bogged down in numbers.

Most founders assume venture capital is the only way to fund their startup, but is it really the right path for you? In this episode of The Backchannel, we challenge the default fundraising mindset, breaking down why so many founders skip critical early steps. We'll shares insights on evaluating your real needs, exploring alternative funding options, and learning from those who’ve been in your shoes. Before you start pitching, make sure you’re not heading in the wrong direction.

In this episode of The Backchannel, I’m sharing some thoughts on goals for the year—what I’m focusing on, what’s working so far, and what still needs improvement. From business to personal challenges, I’m experimenting with new approaches and seeing where they lead. If you’ve set goals for yourself, I’d love to hear them. Let’s keep each other accountable!

How do you convince investors to back you when your company’s growth has been stagnant? In this episode, we explore a question from a founder about breaking through that barrier. We’ll dive into what investors are really looking for, the importance of showing a shift or inflection point in your business, and how to craft a compelling story about the future. Plus, some thoughts on when it’s time to step back and rethink your approach before seeking investment.

In this episode of The Backchannel, Jason reflects on his own fundraising experience and breaks down the layers of what it really takes to secure investor commitments. Using his 2017 fundraise as a backdrop, he shares insights on the role of connections, the limits of those advantages, and why getting your foot in the door is just the beginning. Whether you're a founder navigating the challenges of raising capital or just curious about the process, this episode offers a candid look at the dynamics of building relationships, crafting a compelling story, and making your pitch count.

This episode of The Backchannel breaks down how the expectations for early-stage founders have shifted in the AI era. Inspired by a conversation with Jeff Bussgang—Harvard Business School professor and author of The Experimentation Machine—we explore what venture capitalists are looking for before investing. From validating your idea to leveraging AI and affordable global talent, the bar for getting to product-market fit is higher than ever. If you're building a startup or gearing up to raise funding, this episode lays out what it takes to stand out.

In this New Year’s episode of The Back Channel, we talk about the power of simple outreach and why reconnecting with your network can be the best business development move for the year ahead. Drawing from personal stories and founder advice, we explore the impact of small, thoughtful gestures—like a quick “Happy New Year” note—and how they open doors for future opportunities, from fundraising to partnerships. Whether you're looking to raise capital or strengthen connections, this episode covers practical tips to kickstart your year with intention and momentum.

In this episode of The Backchannel, we ask a critical question for founders: Should you actually be raising venture capital?

We break down why most founders chasing VC money are doing it for the wrong reasons—whether it's validation, peer pressure, or simply not knowing other options. We also explore two common categories of founders who mistakenly pursue VC dollars and share practical ways to rethink your funding strategy.

If you’ve ever considered raising venture capital, this episode will challenge you to reflect on your motivations and explore smarter, more sustainable ways to build and grow your business.

In this episode of The Backchannel, we break down the concept of closing dates in fundraising and why they’re a powerful psychological tool rather than a legal requirement. Learn how closing dates create urgency, push investors to commit, and help fundraisers organize their rounds effectively. Whether you're a startup founder or a fund manager, this episode will help you understand how to set and communicate closing dates to drive decisions and close your round with confidence.

In this episode of The Backchannel, we dive into the trade-offs between maximizing valuation and keeping deal terms simple. Whether you're a founder chasing a higher valuation or an investor protecting optics, adding deal structure can have long-term implications. Learn why simplicity often wins in the end and how complex terms like liquidation preferences, warrants, and dilution protections can create friction for future rounds. Tune in to hear why aiming for a clean deal benefits everyone in the long run.

In this episode of The Backchannel, we explore how to prepare for final VC meetings, what investors are really looking for, and how to handle the pressure of tough questions. Whether you're a first-time founder or a seasoned entrepreneur, this episode is packed with actionable insights to help you close the deal with confidence.

In this episode of The Backchannel, we explore strategies to help a founder turn investor interest into momentum during a challenging fundraise. From avoiding reliance on a single viral moment to showcasing consistent progress, we discuss practical ways to create the perception of unstoppable growth. Whether you’re pitching now or planning your next round, this episode offers sharp, actionable insights for closing strong.

In this episode of The Backchannel, we talk about the realities of raising capital and why many founders may not be ready for venture funding. Instead, we explore the often-overlooked world of angel investing—who angel investors are, how to find them, and how to tailor your pitch to different types of angels. Whether you’re building a billion-dollar startup or a sustainable small business, this episode offers a practical playbook on how to secure early-stage funding.

In this episode of The Backchannel, Jason unpacks why many founders struggle to raise capital in today’s cautious VC environment and offers alternative strategies to keep momentum. Learn how to tap into angel investors, leverage AI, and access global talent to build traction on a lean budget. Tune in to hear how you can turn obstacles into opportunities—and don’t miss the next episode, where Jason breaks down the art of pitching to angel investors.

In this episode of The Backchannel, we explore why making in-person connections can be a game-changer for founders. Recorded on location in Austin, Texas, Jason shares insights sparked by his own travel experiences, focusing on why meeting face-to-face can have a major impact on relationship-building, especially when it comes to securing investments.

In this episode of The Backchannel, we're dropping a quick but essential take on balancing brilliance and likability and how both play into the fundraising game. We revisit a core concept from a past episode: time given – time to interest. If your brilliance gets investors hooked fast, you don’t need as much relationship-building. But if it takes longer to spark that interest, likability becomes your best tool for buying more time. We also talk about how being difficult, even if you’re brilliant, can close doors.

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In this episode of The Backchannel, we're diving into the role anxiety plays in fundraising, especially when it comes to warm introductions with investors. If you’ve ever hesitated to reach out to old contacts or second-guessed your follow-ups, this one's for you.

Jason unpacks the three stages where anxiety can creep in: identifying who to contact, crafting outreach messages, and handling follow-ups.

He offers practical tips to overcome these mental blocks and replace hesitation with confidence, making your outreach more effective and less stressful.

Tune in to learn how to reframe your mindset and make those vital connections without second-guessing yourself.

In this episode of The Backchannel, we’re talking about how VCs need to raise money too, not just startups.

We break down what it’s like for venture capitalists to get funding from limited partners (LPs) and why it’s not always easy, especially for smaller funds.

We also touch on how some VCs don’t put as much effort into fundraising as they expect from founders.

This episode serves as a way to remind everyone that, just like startups, VCs need to always be building relationships and raising money.

In this episode, we dive into the concept of awareness for founders, focusing on how to effectively create it.

We discuss different strategies to build visibility that feels genuine and impactful, rather than forced or overly targeted.

This episode serves as a reminder that it's all about positioning ourselves in a way that naturally draws in interest and makes us stand out for the right reasons.

This kind of awareness ultimately makes all the difference in how others perceive our business, especially when it matters most.

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In this episode of The Backchannel, we talk about handling the pressure of investor pitches.

Many founders feel anxious about facing tough questions from investors, but it’s important to understand that these questions often come from genuine interest, not an attempt to catch you off guard.

We explore why investors ask challenging questions and how to reframe them as opportunities.

We also touch on how your existing knowledge and experience can help you confidently navigate these conversations, even when you don’t have every answer.

The key takeaway: it’s a conversation, not an interrogation.

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In this episode of The Backchannel, we explore the different types of angel investors you’re likely to encounter early on in your startup journey.

We dive into the factors that define these investors—ranging from their wealth to their level of sophistication—and how their motivations shape their involvement.

Whether you’re seeking strategic support or just looking to raise capital, understanding these dynamics can help you navigate which angels to bring on board and which ones to avoid.

Listen in to learn how to approach angel investors and align with their expectations.

In this episode of The Backchannel, we explore the ins and outs of valuation caps and uncapped SAFEs.

Many founders toss around terms like valuation caps without fully understanding their impact, and we’re here to break it down.

We’ll dive into why some investors and founders are drawn to uncapped SAFEs, the potential risks involved, and when this type of funding structure might actually make sense.

Tune in to learn why this approach can be tricky for both sides and how to navigate these waters with more confidence.

In this episode of The Back Channel, Jason tackles the often misunderstood concept of valuation caps in fundraising.

He walks through what a valuation cap is, how it works, and its role in SAFE agreements and convertible notes.

Jason explains how these caps affect the conversion of investments into equity during future funding rounds, and covers the difference between pre-money and post-money valuation caps.

The goal is to help founders better grasp the math behind the numbers, so they can navigate their fundraising with more clarity and confidence.

In this episode of The Backchannel, we revisit a fundamental topic that every founder should understand: post-money cap SAFEs and their implications. Starting with a refresher on the basics of post-money versus pre-money valuations, the discussion then moves into how these financial instruments impact founder ownership and why they can be tricky. Listeners will gain insights into the dynamics of post-money caps, particularly the hidden complexities that can affect a company’s valuation during fundraising. Whether you’re a new founder or just need a refresher, this episode sheds light on the often misunderstood aspects of post-money caps and offers practical advice for navigating them. Listen in to better understand how to protect your stake in your company.

In this episode of The Backchannel, Jason dives into one of the most overlooked yet essential tasks in fundraising: building your target investor list.

He breaks down why so many founders avoid this work—it’s time-consuming, tedious, and can be confusing. But also emphasizes its importance and offers a step-by-step guide on how to tackle it effectively.

From researching top-down and bottoms-up investor lists to mapping out connections and crafting the right emails, Jason covers it all. He also shares tips on how to stay organized and maintain momentum throughout the process.

Whether you’re overwhelmed by the idea of reaching out to investors or just need a solid strategy, this episode has the actionable advice you need to get started.

In this episode of The Backchannel, we dive into a topic that’s been on a lot of founders’ minds: the difference between pre-seed and seed rounds in today’s shifting market.

We explain how the definitions and expectations for these funding stages have evolved, especially after the wild fluctuations caused by events like ZIRP and the SVB collapse.

We break down what VCs are now looking for in pre-seed deals and seed deals in the current market.

We also address common questions, like whether you can use the same pitch deck for both rounds and the role of institutional investors in pre-seed funding.

Listen to the full episode to hear more!

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In this episode of The Backchannel, the focus is on the critical role deadlines play in successful fundraising efforts. Deadlines can create a sense of scarcity and urgency, helping founders manage and control the fundraising process more effectively. By setting clear deadlines for meetings and feedback, founders can signal to investors that there are other interested parties and maintain a balance of power. Additionally, using deadlines tactfully, combining firmness with politeness, ensures they are respected without appearing overly aggressive. Deadlines also help investors prioritize opportunities, ultimately benefiting both parties. Applying the concept of deadlines beyond fundraising can improve overall efficiency and effectiveness.

In this episode of The Back Channel, we explore a critical topic for founders: showcasing traction to VCs.

Jason does another mailbag answering questions submitted by founders worldwide, exploring topics like how macroeconomic conditions impact investor targets, the importance of presenting meaningful metrics, and strategies for highlighting your unique traction.

We also discuss key red flags to avoid and tips on effectively presenting growth without setting unrealistic expectations.

Listen in for actionable insights and advice to enhance your fundraising efforts!

In this episode of The Backchannel, we revisit a popular topic among founders: how to create efficient fundraising processes.

We address several questions submitted by founders, exploring various aspects of the fundraising journey.

Our discussion covers strategies for improving investor outreach, managing communications, and maintaining momentum throughout the process.

We also touch on common challenges founders face and offer general advice on approaching investor interactions.

This Q&A format allows us to provide targeted insights on the specific concerns many founders have when it comes to fundraising efficiently.

If you have questions for us that you want answered in a future episode, make sure to send us an email or shoot us a DM on any of our socials!

In this episode, we're tackling an important startup scenario: unexpected VC interest. We'll be answering a question Jason received from a founder who received an out-of-the-blue email from an investor. We'll also some practical tips on how to handle these situations smoothly, including ways to maintain control of the conversation and your timeline, the benefits of not immediately jumping into fundraising mode, how to research potential investors, and what to prepare (spoiler: less than you might think) for initial meetings. Plus, we'll give you some pointers on transitioning from casual chats to formal fundraising when you're ready. Whether you're new to the startup world or a seasoned pro, this episode has some valuable insights you can put to use.

In this episode of The Back Channel, we dive into five thought-provoking strategies to elevate your fundraising game while challenging existing advice.

We explore concepts like pitch deck templates, riskiness of your idea, seeking rejection, tiering investors, and fundraising preparation.

Join us as we challenge norms and empower you to refine your fundraising tactics effectively.

In this episode of The Backchannel, the focus is on why intelligent individuals often struggle with pitching to investors.

The discussion includes the common pitfalls such as overemphasizing data, battling imposter syndrome, and the tendency to overcomplicate pitches to prove intelligence.

The importance of simplicity, emotional connection, and embracing rejection as part of the fundraising process is  also highlighted.

Overall, the episode provides valuable insights and strategies for intelligent founders to improve their pitching skills.

In this episode of The Backchannel, Jason answers 5 questions submitted by founders about pitch decks and pitching strategies.

During the episode, he highlights the importance of simplicity and clarity in both deck design and delivery.

Jason also discusses balancing design and content, conveying a compelling vision, and avoiding information overload.

On top of that he also touches on effective communication in short pitches and the strategic use of competition slides.

Make sure to listen to hear his full answers!

VC signals can be tricky. A lot of them are deeply intertwined with social dynamics and can change investor interest in a matter of seconds.

In this episode, Jason shares a recent example of how fast negative signaling can impact a deal.

Listen to the full episode to learn about different types of VC signals and how you can use them to help you raise your round!

Welcome back to The Backchannel! In this episode, we're trying out a new format where we dive into your burning questions about how founders should navigate investor passes. Join Jason as he addresses the following questions:

- Should you send a follow-up email after a pass? How soon is too soon to follow up after an informal meeting?
- Is it appropriate to ask for feedback on why an investor passed?
- How soon do I follow up with an investor who seemed interested?

If you enjoy this format, let us know what other topics you'd like us to cover!