In this episode we dive into raising extensions and bridge rounds. Many companies are looking to these as ways to extend their runway, but they can be complicated. How do you go about raising these kinds of rounds? We are here to help! In this episode we answer questions including:

• What is the difference between an Extension and a Bridge round?
• How do I talk to my investors about an Extension?
• What happens if one of my investors won't participate?
• How much should you raise for an Extension?

All of these questions were submitted by listeners just like you. You can submit questions for us to answer on our website TheStartupHelpdesk.com or on X/Twitter @thestartuphd - we'd love to hear from you!

Your hosts:

• Sean Byrnes: General Partner, Near Horizon www.nearhorizon.vc
• Ash Rust: Managing Partner, Sterling Road www.sterlingroad.com
• Nic Meliones: CEO, Navi www.heynavi.com

Reminder: this is not legal advice or investment advice.

Q0: What is the difference between an Extension and a Bridge round?
Extensions and bridge rounds are the same: you’re raising a smaller amount before the next priced round, instead of an actual priced round. There are 2 reasons to do it: a position of strength or weakness. Weakness is the most common situation and you will see people use the term "bridge round" more often here. The term "extension" sounds better, so you should always use that.

When pursuing this type of round, usually you have not grown as fast you would like and thus need more time to hit the milestone needed for the next round. That time requires a little more money.

When pursuing an extension from a position of strength: you have grown very quickly, your existing investors are desperate to add more to their investment and you only need a relatively small amount to skip the next round completely.

Q1: How do I talk to my investors about an Extension?
You really don’t want this to be the first time they hear the news. Make sure you send regular monthly updates to your investors. This makes a huge difference in investors' willingness to help. Make a basic plan first, with the projections and expected outcomes: the extension should prepare you for a great priced round or liquidity event. Then, contact your friendliest folks first and build momentum.

Investors say "no" via email all the time to founders. It is important to break through the noise. Call your investors or meet them in-person to ask for their participation in the extension.

Q2: What happens if one of my investors won't participate?
This is a very common problem. Close the yeses now. A SAFE is one of the more common funding methods for this type of round. Then, you have to decouple the dependencies. Does this investor have real concerns and obstacles? Does this investor just not have the cash to allocate to the extension?

If you cannot get this investor to participate in the round, start rallying new investors. Consider alternatives such as crowdfunding, too.

Q3: How much should you raise for an Extension?
What's your next milestone? Agree on that first. Then: how much cash do you need to reach your next milestone?

Aiming for 12+ months of runway is not a bad way to frame it, but milestones are more important. Is there a critical revenue milestone that you are approaching? Is there a key growth milestone that this extension can help you achieve? Investors want their cash to be fuel for reaching major milestones. Identify the right milestone, and map out how much cash you need to reach it. With that number in hand, remember that you almost always need more funding than you think to reach a given milestone.

In this episode we dive into category creation and what it takes to win in a new category. Many startups are building products unlike anything that has existed before, but how do you build a category around it? How do you let people know it even exists? We are here to help! In this episode we answer questions including:

• What is category creation?
• How do you anticipate the need for a new category?
• How do you educate the market that your new category exists?
• How do you maintain a competitive advantage as your category grows?

Sean Byrnes has co-founded, scaled, and sold multiple startups and has invested in and advised countless others. "Category creation" has been central to Sean's ability to go from 0 to 1 and beyond. Ash and Nic put Sean on the hot seat to unlock winning strategies around category creation.

All of these questions were submitted by listeners just like you. You can submit questions for us to answer on our website TheStartupHelpdesk.com or on X/Twitter @thestartuphd - we'd love to hear from you!

Your hosts:

• Sean Byrnes: General Partner, Near Horizon www.nearhorizon.vc
• Ash Rust: Managing Partner, Sterling Road www.sterlingroad.com
• Nic Meliones: CEO, Navi www.heynavi.com

Reminder: this is not legal advice or investment advice.
Q0: What is category creation?
If you are selling something where there was nothing like it before, it’s category creation. This differs from a "replacement": selling a product that replaces something else (a product, person, role).

Q1: How do you anticipate the need for a new category?
Category creation starts with problems. You may observe old problems that go from small to huge (SaaS). Another way for opportunities to emerge is from problems that arise through new technologies, markets, or changes (mobile apps).

“What kinds of problems are increasing in pain but now may be solvable given this shift?” These opportunities all start with inflection points: something needs to change to disrupt the status quo.

Creating new categories is usually not the best approach. Even if it is, it often takes years before people recognize that the category exists.

Q2: How do you educate the market that your new category exists?
While replacement products are all about competitive advantages, category creation is all about education.

Most of the education is not about your product. Instead, educate your prospective customers that it’s possible to solve the problem! You just want everyone to know that solutions exist. Teach people what to look for in solutions: give them criteria and teach them how to evaluate.

With “education” as a central component of your strategy, you still need to stay true to your classic startup principles: validate that people have a need, show them a clear use case, and generate proof that prospective customers want it badly.

Q3: How do you maintain a competitive advantage as your category grows?
First mover advantage is a fantasy. You would much rather be second or third. If you do create a category, there are a few advantages you can build up:
- Premium customer logos.
- Create your own conferences.
- Prime positioning with analysts/industry coverage.
- Defining the industry standard.

Treat customers like co-researchers on this emerging frontier. Earned and owned media builds trust and buy-in.

Lightning Round
How do you validate demand for this type of startup? Is it different in any way than the classic methods that startups should take?

What’s more important: a crystal ball type of ability to anticipate a new category of opportunity or the ability to iterate quickly when an opportunity

In this episode we dive into new kinds of Venture Capital firms and what they offer startups. Many startups seek venture funding, but most funds look the same. What can new types of funds offer? When are they a good fit for you? We are here to help! In this episode we answer questions including:

• How involved should a typical VC be?
• What’s more important the founders or the market?
• What are examples of an “unfair advantage” that a startup can have?

We also hear details on Sterling Road and Near Horizon, two new kinds of venture firms started by our own Ash and Sean!

All of these questions were submitted by listeners just like you. You can submit questions for us to answer on our website TheStartupHelpdesk.com or on X/Twitter @thestartuphd - we'd love to hear from you!

Your hosts:

• Sean Byrnes: General Partner, Near Horizon www.nearhorizon.vc
• Ash Rust: Managing Partner, Sterling Road www.sterlingroad.com
• Nic Meliones: CEO, Navi www.heynavi.com

Reminder: this is not legal advice or investment advice.

Q1: How involved should a typical VC be?
For a typical investor, they should not be involved much at all. Many VCs don’t have experience operating a startup, thus, their advice can be distracting. Nonetheless, it is important to keep them regularly tuned in via monthly status updates.

For investors that have built and led startups, their help can be significantly more meaningful. With Sterling Road, Ash provides regular cadence coaching to help your startup at the earliest stages. This also includes hiring intros, customer intros, community access, and fundraising help.

Sean explains that Near Horizon gets as involved as possible, but they aren’t the CEO. You need a CEO with vision and deep knowledge of the space; Near Horizon is the booster rocket to make them better. They support the CEO with a wide range of founder-centric efforts, but fundraising and hiring remain the CEO’s responsibility.

Q2: What’s more important the founders or the market?
You need both! The table stakes for a startup:
1: The market: it needs to be a huge problem with a lot of potential buyers.
2: The founders: impressive founder with a history of success and resilience is key. The founder will make or break the company.
3: Proof: then you need a great idea, evidence that it might work, a demo, and a bunch of customer discovery.

Great founders can build businesses in small markets, but not venture-backable businesses. Weak founders can show traction in big markets but will struggle to scale. Investors are looking for a unicorn, and that is very rare. Most investors review hundreds if not thousands of startups for every one investment.

Q3: What are examples of an “unfair advantage” that a startup can have?
Ash explained that Sterling Road prizes advantages in tech, network effects, and user experience (usually based on tech, otherwise a competitor could easily copy it).

Sean emphasized that Near Horizon looks for founders with unfair advantages in distribution. You need a way to reach your customers that isn’t paid advertising.

Other nice-to-haves include:
Hiring - having a network of amazing people who want to join your team.
Customer rolodex - knowing the first dozen or so buyers.

Lightning Round

• Do founders make the best investors?
• What’s a clear indicator from a startup that can make it interesting to potentially invest?
• After three months of receiving the Near Horizon or Sterling Road golden touch, what’s the change that a startup should experience – what can they now do differentl