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!