Paul G. Silva

MARCH 26, 2020

This post cover the Beginner (101) level best practices for crafting strong startup presentations. Multi-person pitches add complexity that almost always leads to people going over time, stepping on each other, or confusing the audience. Would you walk into a room of English speakers and do your pitch in Russian? Of course not!

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This is going to be BIG.

JUNE 22, 2020

One of the most difficult conversations I have with founders is when they haven’t quite given me enough of a story for me to make a proper evaluation. If I wind up asking for more info, it might result in a founder feeling like they’re getting the runaround, given what the founder believes to be an obviously good idea.

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Dream It

SEPTEMBER 25, 2020

Among them, VCs and startups are forced to interact remotely and make deals without ever shaking hands. Many of these new red flags that occur during virtual pitching are easy to fix. In this Dreamit Dose, Healthtech MD Adam Dakin provides 5 simple rules to avoid giving investors the wrong impression when pitching remotely.

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This is going to be BIG.

AUGUST 30, 2020

Talk to ten founders and ten different VCs and you’ll get roughly about 600 different suggestions as to how you should go about your fundraising strategy. Too often, founders look at what they’ve done so far as proof they should get funded, whereas they should really be looking at it as proof of a funding-worthy plan. What gives?

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Dream It

JULY 31, 2019

Being self-sustainable has given us a new perspective on startup funding, especially compared to what I experienced on my first accelerator run. The press enhances this misconception around YCombinator demo days, where the 3-day pitch event is perceived like an auction, with investors fighting each other for the best deals.

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This is going to be BIG.

FEBRUARY 21, 2021

I’m a female founder. I don’t have a technical co-founder. These are all of the things I heard from a founder that I recently backed. She was pitching for a pre-seed round of $400k. So what about all of the above statements—things that founders widely hold to be true barriers to fundraising? This isn’t surprising.

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Both Sides of the Table

AUGUST 30, 2014

Many startups now go through accelerators and have mentors passing through each day with advice – usually it’s conflicting. There are bootcamps, startup classes, video interviews – the sources are now endless. What is a founder to do? Improving startup productivity ? Startup psychology / confidence ?

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Dream It

FEBRUARY 27, 2020

But founders are often so consumed with talking metrics, milestones achieved, or the capital they need that they sometimes forget to talk about their overarching vision for their startups. Selling a compelling vision is so critical that some investors weigh it more heavily than the pitch deck itself.

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This is going to be BIG.

JUNE 9, 2020

While I got some very kind words on my recent writings , I heard from some founders that didn't feel like they got treated fairly—specifically around feeling patronized or dismissed—and that I wasn't showing enough action to improve on that. Founders from communities of color are less likely to have personal wealth to fall back on.

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This is going to be BIG.

OCTOBER 28, 2016

Startup failure comes quick and often messy--great for storytelling. The Coveteur article featuring Andy and Bonobos encapsulated exactly how a founder worth writing about will act: ".He 4) Thank Andy Dunn for showing us the way to be one of the best storytelling founders ever. And it’s true: [FOUNDER] is wildly successful.

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This is going to be BIG.

AUGUST 25, 2023

It’s your job as a founder to find out the specific risk associated with that attribute and to find out if the reason given is the only reason. But if these people are willing to come on without the co-founder title, that’s between them, you and their employment contract. Let’s first talk about the definition of a co-founder.

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This is going to be BIG.

FEBRUARY 12, 2014

Sometimes it means establishing founder credibility over time to prospective future investors or to potential employees. Here are five aspects of PR I feel like most startups need to do more of: 1) Fit all PR into a long term plan. That doesn''t always mean public press, nor does it mean telling everything about your product.

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This is going to be BIG.

JUNE 17, 2024

Yet, everyone’s got an opinion about how a company measures up, especially the founder. ( The other day, I had a difficult conversation with a founder who clearly felt like VCs were the problem in her fundraising process. I don’t need to remind such a founder how the world is stacked against them. Then, there are nuances.

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Entrepreneurs' Organization

DECEMBER 15, 2021

He has raised venture capital for his startups, helped hundreds of founders craft their pitch decks and fundraising strategy, and invested as a business angel. We asked him how founders can create the perfect pitch deck for their company. Today I am sharing my five quick steps to building the perfect pitch deck.

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This is going to be BIG.

MAY 26, 2022

“Personal Branding” The term is fingernails on a chalkboard-level cringe for many of the best founders—mostly because it feels most of the people who spend time building their personal brand don’t actually have much there there behind it. Unfortunately, this has real consequences for founders. So how can founders differentiate?

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Both Sides of the Table

NOVEMBER 3, 2015

They originally pitched us with a hacked but super productive prototype they built in their fraternity room and a rendering of a beautiful bookshelf sized in-home growing system that they committed to building. One of the first bets we made in Agtech was Grove started by two young, passionate engineers out of MIT – Gabe and Jamie.

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This is going to be BIG.

MAY 5, 2015

So I asked a few founders that I've worked with and they mentioned a word that struck me--because I've never heard any of the hordes of people in my inbox asking for internships, VC job recommendations and advice, etc. People always tell me how smart they are or how much experience they have--or why they have a passion for startups.

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This is going to be BIG.

JULY 22, 2015

We stayed in touch, doing a couple of tris together, chatting about startups, and venture, life, etc. So when we grabbed dinner about a year ago and he told me he gave notice, and that he had a guy working on a thing (that guy was his co-founder Andrew Childs ), I just said "I'm in."

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This is going to be BIG.

OCTOBER 1, 2014

That means that out of nearly $51 billion in funding that startups received over those two years, a comparatively teeny $1.5 Right this very moment, I''m in the process of leading investments in two companies where I had to convince a team with a female founder to take capital. billion went to women-led ventures.". Sounds awful, right?

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Entrepreneur's Handbook

APRIL 24, 2021

Advice for non-technical founders for finding a serious CTO for your startup Finding a co-founder is hard work. Finding a technical co-founder is even harder. Yet, the benefits of having a technical co-founder make it all worthwhile. A good co-founder will serve as a powerful force multiplier.

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This is going to be BIG.

FEBRUARY 17, 2020

We’ve all heard the anecdotes—the famous founder who pitched 1000 investors before any of them said yes. Most founders I know who are in this mode simply haven’t done enough homework and planning on the idea. 3) Have you pitched a critical mass of investors of the right stage and sector?

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Both Sides of the Table

JULY 7, 2015

I love how open Danielle has been throughout the development of her startup Mattermark including honest reflections of when she has changed her opinion. Another founder … “When I pitched the idea to Adam, he was super on board,” Mr. Sloyan said. If anything it felt like a public service to founders to me.

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Dream It

FEBRUARY 1, 2022

When pitching a potential investor or customer, time is of the essence. During Q&A, both sides start engaging in a sort of conversational dance - with one side leading (VC/customer) and the other side following (founder). Treating Q&A as a One-Way Street Founders can take a firing squad approach to Q&A.

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Both Sides of the Table

SEPTEMBER 28, 2013

For starters let me use “CEO” as a proxy to include her “inner circle” which might mean co-founders or might just mean senior execs of the business. The Mind of the Founder. So as a startup CEO you constantly have to suspend disbelief. The mind of a founder is wired differently than most people.

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Dream It

APRIL 8, 2020

Jason sat down with Steve Barsh , Managing Partner of Dreamit, to give founders relevant downturn strategies. Jason answers critical questions for founders, including: How can your company ensure survival? Your primary job as a founder is to save the business. What do investors like Jason want to see from founders?

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This is going to be BIG.

NOVEMBER 17, 2014

They''re new to the gig, super excited about all its potential, and getting out there selling founders hope for that one big gamechanging deal. They just move too painfully slow to work with startups. That''s really all I have to give to the founders I back. It takes longer to get to know the founders. quicksand.

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Both Sides of the Table

FEBRUARY 22, 2015

After seeing Chamillionaire interact with several entrepreneurs both at events and as an investor I started introducing him to startups in an advisory capacity. It always started the same way – a founder would ask for an intro because they figured he could help with promotion. Startup Lessons' Welcome to the family.

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This is going to be BIG.

SEPTEMBER 8, 2014

Because, you know, who doesn''t love a good startup list. It''s a story of a mechanical engineer turned startup entrepreneur who has seen how NYC actually works (and built a company to help it run smooth) from as deep undergroud as the East Side Access Project under Grand Central and as high as the roof of the NY Times building.

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This is going to be BIG.

JULY 8, 2019

Running a startup consumes a ton of time. Just the immediate priorities seem to take up more than one person’s potential working hours—so it’s no surprise that when it comes to something like social media, many founders have trouble making it a priority. Does just randomly posting on Twitter mean an automatic Series A?

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This is going to be BIG.

MARCH 24, 2014

These days, there are a ton of options for you if you''re a startup seeking guidence. We''ve done a lot to make sure startups get all the help we can get--and it''s leading to higher companies getting off the ground. Not every VC used to get pitched by VC funds for a living and has seen hundreds and hundreds of VC pitch decks.

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Both Sides of the Table

MAY 9, 2018

This is a very common scenario when entrepreneurs pitch VCs and frankly is a very common scenario when VCs try to raise money from LPs. When you pitched me I really did love you. I left the meeting and had to attend a 3-hour board meeting where two founders have been fighting and each want the other one fired. That wasn’t you.

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Revolution

JANUARY 27, 2025

Reflections on Georgetowns 2025 pitch competition from TedLeonsis Last week, Georgetown Universitys McDonough School of Business once again became a launchpad for the next generation of bold thinkers and doers. startup ecosystem. Theyre diverse, resourceful, and both practical and ambitious.

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Dream It

MAY 19, 2021

Seasoned founders have a particular way of answering this question. In this Dreamit Dose, Managing Director Adam Dakin presents his view on the right way to answer it after hearing hundreds, if not thousands, of founder pitches. This should be stated at both the beginning and end of the pitch.”

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Paul G. Silva

FEBRUARY 25, 2025

How Iteration Transformed Valley Venture Mentors Before I co-founded Valley Venture Mentors (VVM) and for all of my time there, we experimented with different ways to connect startups with mentors. Iteration #1: High-Value, but Unsustainable Our first approach was simple: hand-match startups with mentors for one-on-one meetings.

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This is going to be BIG.

JUNE 16, 2014

It''s also not the best way to create a helpful syndicate of investors that share the founder''s vision for the company. If all my deals came as intros from trusted connections that I know for years versus at founder pitch events that''s interesting data. Fear not, founders. That was three years earlier. Five months?

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Both Sides of the Table

JUNE 30, 2016

Amongst the most often asked questions I get from founders is, “How much money should I raise?” Reflexively founders want to raise as much money as they can because they figure it will give them more resources, better chances of competing and a longer runways before they have to do the often painful job of asking, yet again, for money.

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This is going to be BIG.

MARCH 17, 2014

Here are two contrasting startup stories I''ve seen firsthand. With one company, a founder and his super inspirational, creative, and established buddy hatch a plan to build a very strong content brand that serves as a platform for a lot of diverse revenue streams--events, ecommerce, advertising. How is that story being told?

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