Ben Wiggins - Founder & Managing PartnerSubstack

Ben Wiggins Investor Newsletter

Weekly investor insights and AMA responses. Questions from The Founders' Group community, answered here.

Subscribe on Substack

Recent Issues

1

Investor AMA: Low-CapEx vs. High-CapEx

Anush from the Founders’ Group asks: How do investors view and how do their evaluation metrics change when they are looking at a software based startup vs hardware-based/manufacturing/physical product...

CapEx vs OpExSoftware metricsHardware metrics
2

Investor AMA: Words and Phrases to Use and Avoid with VC

Adam from the Founders’ Group asks: What key words and phrases are VC’s listening for that would pique their interests, and any to avoid as Red Flags? VCs are pattern recognition machines. They sit th...

VC storytelling signalsTraction metrics and unit economicsProduct iteration and learning velocity
3

Investor AMA: The 12 "VC Clauses of Death" That Should Kill the Deal

Nitesh from the Founders’ Group asks: What is your take on liquidation preference ? I have heard of some VCs asking for a liquidation > 1x the capital, which doesn’t sound like a good deal for the sta...

term sheetsliquidation preferenceanti-dilution
4

Investor AMA: An Agentic Back Office for Property Management

Chizi in our Founders’ Group ( apply here ) asks: So as we’ve evolved our platform micro MVP, we’ve shifted from a one-size-fits-all contractor platform to offering tailored, kit-like agentic back off...

pricing strategygo-to-marketmarket segmentation
5

Investor AMA: Designing a WINNING Business Model

Corbin from the Founders’ Group asks: How do you design a winning business model that investors will invest in? AMBITIOUS! I love it. Let’s dive in. Photo by Chase Baker on Unsplash I’m not breaking n...

Business model designCustomer discoveryThe Mom Test
6

Investor AMA: Concrete Product vs. World-Changing Vision

David from our Founders’ Group Discord asked the following: Hey everyone, I’m at a critical branding crossroads and would love to get the group’s take, especially from storytellers like Ben. [Thanks!]...

Branding strategyProduct vs Platform narrativesFunding paths
7

Investor AMA: When To Go Full-Time

Adam from The Founders’ Group Discord asks: When is the right time to go full time? I have heard different perspectives on this. Personally for myself I believe if I can get started with 30% of what I...

founder funding decisionsrunway and employment strategyrisk de-risking in startups
8

Investor AMA: Macro Trends to Account for in Investing; Any Irrational Aspects to my Approach? :D

Fabio from our Founders’ Group Discord (Founders apply here , Investors DM me) asked the following: What macro aspects (trends, hot verticals, geopolitics, etc) , do you take in account for investment...

Private marketsMacro investing indicatorsAI investment dynamics
9

Investor AMA: How Do I Judge Investments?

Photo by Towfiqu barbhuiya on Unsplash I recently announced an investment (read about it on LinkedIn here if you like) and Suman from our Founders’ Group Discord asked the following: How did you judge...

venture investingfounder due diligenceunfulfilled demand
10

Investor AMA: Exit Strategy and the Big "Zoom-Out"

Anushrot from our Founders’ Group Discord asked this question: As a former founder, how and why did you exit? Did you have plans to grow it more, diversify, etc.? My plan is to use my product as a ste...

exit strategyacquisitiontraction / product focus
11

Investor AMA: How to Value Your Time

Jules from our Founders’ Group Discord server asked the following question: How much should you value your time as an entrepreneur? Should you consider an hourly rate or salary when asking for funds f...

Founder compensationTime valuationCash flow management
12

Investor AMA: When to Expand Your Team

Adam on our Founders’ Group Discord (ask me for the link!) sent this question. When do you believe is the right time to expand your team? I read you should hire in areas you have a weakness or lack of...

Hiring strategyEquity compensationCompany culture
13

Investor AMA: Evaluating a market where large public player stocks are falling

Suman on our Founders’ Group Discord sent this question. I am building something related to online dating but the stock prices of current giant like match group is too much down, should i consider thi...

market size and growthmonetization strategyAI safety and trust features
14

Investor AMA: To hire BD or not to hire BD?

Here’s another question from Refael (@rpal7511 on the Founders’ Group Discord):: Do I need some one separate as the BD [business development] guy in my venture? The founders know their product and got...

Business DevelopmentFounder RolesGo-To-Market
15

Investor AMA: Questions on How to Choose the Right Venture

Today we have a question that turns into two questions, from Refael (@rpal7511 on the Founders’ Group Discord): You answered from an investors perspective, I ask from the worker or even co-founder per...

Market selectionCo-founder dynamicsStartup governance and conflict
16

Investor AMA: Questions on Founder Capital Mistakes, Investing in Emerging Markets, and Transition to Founderhood

Question from Abdulshakur Silvester within our free founder/investor group (message me for an invite, we have 350 founders and several dozen investors in a Discord, all free)… What are the biggest fin...

Fundraising mistakesEmerging markets investmentFamily offices vs venture capital
17

Investor AMA: Question on Evaluating Founders

Question from within our free founder/investor group (message me for an invite, we have 350 founders and several dozen investors in a Discord, all free)… As an investor how do you evaluate your confid...

Founder evaluationFounder traits (curiosity, coachability, commitment)Traction and pre-sales signals
18

Investor AMA: Question from a Young Founder

A young founder recently asked me: Hi again! I’d love to share more about my story with you. I’m 13 now, but I’ve been curious about tech and online communities for a few years already. In the beginni...

early-stage entrepreneurshipfounder mentorshipconsistency/persistence