Inside Demo Day at Iterative: What Founders Need to Know

Inside Demo Day at Iterative: What Founders Need to Know

Yi Jun Phung
May 29, 2024

One of the most popular questions we get asked is: What is Demo Day and how does it work?

Demo Day at Iterative is where founders of the batch pitch to a large group of investors across SEA, Asia Pacific and the US. It consists of the Alumni Demo Day Virtual Event, Demo Day Virtual Event and the Demo Day Website. All of these happen at the end of the batch, twice a year.

Founders often see huge progress and momentum during the program (growing 5-7% per week is integral), and Demo Day is an opportunity for founders to pitch their startups to investors to ramp up on their fundraising journey. Companies in our program have gone on to raise $168M collectively.

To help, we've split this article into two sections:

  • Preparing for Demo Day - How we help founders gear up for Demo Day.
  • Demo Day - Diving deeper into the 3 components of what makes up Demo Day.

Preparing for Demo Day

The last month of the program is focused on helping companies prepare for Demo Day. We run a four-week Fundraising Bootcamp where we…

  • Teach founders what we’ve learned about fundraising
  • Work with companies on their pitches
  • Have them practice their pitches in groups
  • Introduce them to investors

The fundraising bootcamp is a pivotal point in the program. For the first two months, we strongly discourage founders from thinking or working on fundraising - they should only work on their startups and focus on growing. It's only when fundraising bootcamp kicks off where the founders go into fundraising mode, and they go from no work on fundraising to lots of work on fundraising.

To be clear, the bootcamp doesn't mean the founders pause on the growth of the company - we're still helping founders to hit their 5-7% weekly growth rate as they also work on fundraising.

To help founders prepare, there are 3 activities we host:

  • Fundraising Bootcamp Kickoff
  • Pitch Practices
  • Friendly Investor Pitches

Fundraising Bootcamp Kickoff

Bootcamps, as per definition, are short, intense and rigorous. To make the most out of the bootcamp, it's important to first arm founders with knowledge on fundraising and how to be effective at it. It's why we host a kickoff at the start of the bootcamp - think of it like orientation for the fundraising bootcamp where we set expectations for the next 4 weeks.

The kickoff also fills in knowledge gaps for our founders. Iterative invests from early-stage to seed stage, so the founders’ understanding of fundraising varies.

How It Works

In the kickoff, Brian and Hsu Ken share everything they've learned about fundraising successfully, from creating a compelling pitch to managing investor interest. Brian and Hsu Ken are founders who have fundraised successfully in the past (Brian raised $200M Series D for Divvy Homes) - and we think it's important for founders to hear from people who have actually fundraised well before. Fundraising is brutal, and only someone who has fundraised before knows the brunt of it.

Brian and Hsu Ken also often tell founders there is no magical solution or trick to make fundraising easier. Fundraising is always going to be hard, but it is a useful skill anyone can learn.

In the kickoff, they cover fundraising topics from the start to the end, from preparing for a fundraise to closing the deal. Some key topics:

  • Understanding Venture Capital - Fundraising is like sales, and in order to sell, you need to know who you're selling to. Brian and Hsu Ken share more about understanding investors and how they operate.
  • Effective Pitch - Storytelling is a crucial part to fundraising. The bootcamp covers the elements of what makes an effective pitch.
  • Create Effective Process - Preparation is only half of the battle. For a successful fundraise, founders also learn how to create an effective process that generates the most investor activity in the shortest amount of time possible.

Alumni of Iterative have shared with us that the materials at kickoff is a resource they come back to from time to time. Founders will continuously fundraise as their startups grow, and everything they've learned more than likely can be applied in the future.

Pitch Practices

Almost all of the successful pitches you see online went through a lot of iterations. Similarly, our pitch practices are designed for founders to create their pitch, get feedback, iterate, and refine it.

The key here is to iterate and figure out what works (or doesn't). Hsu Ken always compares it to comedians practicing their craft. When it comes to comedy, it's not just about writing good jokes, but it's also about the delivery, timing, and energy. To get it right, comedians like Chris Rock don't start at the big arena - they go to small comedy clubs and tell the jokes to family and friends. They practice, again and again. They see what jokes made people laugh, which fell flat, and try different deliveries to see the audience's reactions. Once they have enough data, they move on to the big arena with a list of things they know will work.

How It Works

After the kickoff, founders work on creating their pitch outlines. They then present during pitch practices.

We host four pitch practices each week. The founders are separated into smaller groups, and each company takes turn to pitch for 3 minutes. Founders get immediate feedback from other founders, Visiting and General Partners.

The reason why founders are broken into groups (and they don't just pitch individually to the General or Visiting Partners) is because founders learn a lot from hearing (1) how other founders pitched (2) the feedback other founders received. Even if the feedback is not for them specifically, it's helpful to hear pointers that can help them refine their own pitches and to avoid common mistakes.

After gathering feedback, the founders continue to work on the pitch until the next pitch practice session. Again, founders have four pitch practices until Demo Day.

We notice that pitches almost always improve as the weeks go by. As Brian and Hsu Ken shared before: Fundraising is a skill, and like any skill, anyone can become better at it.

Friendly Investor Pitches

Friendly investor pitches are an opportunity for founders to have the experience of pitching to a real investor. It's also an avenue for founders to continue improving their pitch as they'll hear different perspectives and opinions from the investors.

How it Works

Each founder pitches to 3 friendly investors. Each pitch is 20 minutes. Founders get 3 minute to pitch and for the remaining 17 minutes, they receive feedback on their pitch.

We match investors with the founders by industry (AI, Fintech etc). Sometimes investors also let us know which company is better suited for their expertise.

These friendly investors come from Brian and Hsu Ken's network.  For the Winter 2024 batch, Piruze Sabuncu (Square Peg), Dhiraj Mukherjee (Co-founder of Shazam), Nicolas El Baze (Partech) gave our founders feedback on their pitches.

Demo Day

The actual Demo Day consists of these three components:

  • Alumni Demo Day Virtual Event
  • Demo Day Virtual Event
  • Demo Day Website

While the actual event is the Demo Day Virtual Event, we consider the Alumni Demo Day Virtual Event and Demo Day Website to be part of it as the former is the dress rehearsal, and the latter is what generates the most connections.

Alumni Demo Day Virtual Event

The Alumni Demo Day Virtual Event is a dry rehearsal, which typically happens 2 days before Demo Day Virtual Event. Only alumni of Iterative attends as the audience.

How It Works

It runs exactly the same way as Demo Day Virtual Event! (See Demo Day Virtual Event below). We host Alumni Demo Day Virtual Event because of 3 reasons:

  1. Familiarise with event - Founders get a feel of how the Demo Day Virtual Event will go. They get to familiarise themselves with the flow of the event and take note of hiccups that could occur.
  2. Go through run of show - The Iterative team tests the platform we're using to make sure everything runs as intended and to catch any technical errors early. We want to make sure it's a smooth experience for attendees.
  3. Alumni as test audience - Alumni have been through Demo Day before, and therefore are the best people to be the test audience for founders in the batch. They share great feedback and give pointers on how to best answer questions from investors. It's typically an encouraging environment where the alumni cheers the batch on and gives helpful advice.

Demo Day Virtual Event

The Demo Day Virtual Event is where founders pitch to a large group of investors, helping our founders get maximum reach. It's held virtually, which means investors across the globe can join easily. For batch W24's Demo Day, 400+ investors signed up for Demo Day.

How It Works

The event kicks off with a short introduction from Iterative, before transitioning to the pitches. Founders get 3 minutes to pitch, followed by a round of live Q&A for 1.5 minutes. Investors ask their questions via the chat function, and Brian and Hsu Ken acts as the medium during the Q&A. After all of the company pitches, we ask investors to connect with founders via the Demo Day website.

The Demo Day virtual event is for investors only - we do due diligence and only allow approved investors to attend. This is intentional because (1) effective fundraising requires founders to talk to a lot of investors in a short amount of time (2) founders’ time is limited and we'd like for our founders to engage with only investors.

Demo Day Website

The website makes it easy for founders and investors to connect. The website is also made available for investors who were unable to make it. They can watch the recordings of the pitches and connect with founders too.

How It Works

The website is populated with the company's information and the pitch recordings from Demo Day. There are also two buttons - "Show Love" or "Connect About Investing" - they're meant to signal an investor’s interest in the company. Clicking on either button will send an e-mail to the founder showing the investors’ interest.

When Demo Day ends, founders follow up with these investors. Founders can also ask Iterative for investor introductions. If they are warm and within our network, we can help make the connection. The website generates the most activity and connections between founders and investors. In the past, we've made 300+ introductions.

Similarly, only investors and founders have access to the website. We'd do due diligence and only give approved investors access.

Opportunity for Founders

Demo Day is an opportunity for founders to pitch and reach a wider network of investors. Our network spans beyond SEA, from the US to Taiwan. It's the start of our founders’ fundraising journey and helps them get maximum reach.

We also think of Demo Day as an advantage for founders - it puts them in front of a group of investors who are keen to hear about the next big thing.

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