From $100k -> $75M - this week's fundraising lessons

Good morning!

Welcome to another edition of the Product in Public newsletter, where I give you an inside look at how I help companies attract capital and build better products.

Today I'm sharing some lessons from working with two companies that were fundraising vastly different sums of money.

If you want the short version, check out the summary below. Otherwise, scroll down for the TLDR version.

As always, thanks for being a subscriber!

Summary of today’s post

  • The amount of money you can raise is dependent on the phase of growth. Ex. seed stage startups should not be attempting to raise more than a few million dollars.
  • Storytelling is critical to designing an attention grabbing pitch deck. If you aren’t versed at storytelling, you need to outsource your design efforts.
  • Passing on revenue opportunities can be hard. But, it becomes easier when you recognize the likelihood of earning the revenue you are envisioning.

A tale of two fundraisings

This week I had the opportunity to look at two different fundraising opportunities totaling $75,100,000 in capital.

That is a whole bunch of moneHere are!

What’s interesting about that total is the disparity in the size of each deal. One founder was looking for $75,000,000 for their startup and the other was looking for a mere $100,000 for their startup.

In working through each of those opportunities, I noted a few lessons that I want to share with you.

Although there are some unique points, today’s lessons can apply to just about any startup looking to raise capital. So, make sure to take notes.

Fundraising opportunity #1 - $75,000,000 in equity funding (investors)

This was a startup in a space where I have not seen a lot of requests for fundraising - agtech, or agricultural technology.

This particular company was making a play in the mineral space. Here are a few things I noted with this opportunity that might prove helpful for you to note.

  1. Their ask was way too big for an initial round of funding.

The average seed round, based on my direct experience, caps out at around $1M-$2M. This ask isn’t off by just a 10x factor of that, they are off by a 35x factor. Few investors are going to give a company $75M at the seed stage.

  1. Understand your target investor.

This point is similar to #1, but I wanted to drill deeper into one aspect.

I was honored to be asked to help this startup fundraise, but looking back I was the wrong consultant to ask. Why? Because all of my investor contacts are angel investors. I have venture capitalists and private equity contacts, but I focus on deals that angel investors would be interested in. First, because I am an angel investor myself, and second because that is where I feel like I can add the most value.

When you are fundraising, you need to be very targeted with the type(s) of investors you are seeking. By showing your deal to the wrong investors, and consultants who have the wrong investor contacts for your type of deal, you are wasting everyone’s time including your own.

  1. More startups are terrible at storytelling.

Although I’m focused on these two deals, I looked at a third deal this week that had the same challenge - the founders were terrible at telling the story of their startup.

For this larger opportunity I received 5-10 documents, each outlining various aspects of the opportunity. Every single one of them was far from concise and efficient in their storytelling. The biggest issue this large opportunity had was that they used super generic language. So much so that I had a hard time understanding what they were building.

I often see this with startups where the founder(s) have science backgrounds rather than business.

If you don’t have someone on your team who is great at storytelling, both orally and visually, hire someone to help you craft the story.

After testing the waters with a few investors, I eventually decided to pass on this opportunity. The chances of them successfully closing a round of funding were low in general and I didn’t feel like my investor network was right for this opportunity.

Some people might struggle with the idea of passing on a $75M deal. After all, such a deal could be worth upwards of $1.5M to my business.

But, it wasn’t a hard decision, because I know my target market and when I can/can’t add value. This was one of those instances where I was going to put in a lot of work with a super low probability of gain.

Fundraising opportunity #2 - $100,000 line of credit

Opportunity number two came via referral from a banker. His financial institution was not able to help this startup because of their limited length of time (the business was less than one year old).

While it’s common for a traditional bank to want to see two years of experience in business, I still believed that getting approved for a line of credit, with other lenders, was viable.

There were a few reasons why:

  • The founder had successfully exited a prior business.
  • They had a ton of experience in their industry.
  • There was already close to $1M in revenue, in less than one year.
  • Multiple contracts for additional revenue had recently been executed.
  • The industry the business was in, government contracting, is one that the SBA likes.
  • The founder was a veteran and the SBA has programs specifically for veterans.

With all of that going for the business, I thought there was a real chance to help this startup.

However, I eventually had to pass on this opportunity as well.

Here’s why:

  1. the opportunity is smaller than my typical deal size.

I only work on deals that are $500k or larger. I did put some time into trying to source this deal, but only because it was a referral from a new referral source (thanks Michael!) and I wanted to try to be helpful.

  1. the founders weren't open to the most viable loan type(s) for their situation.

Since the business was so new and the business had multiple contracts signed, the vast majority of lenders leaned towards invoice factoring. This is a more expensive type of financing that the founder was not open to exploring.

I completely understood his stance. Again, factoring can be expensive. But, when a business is so new, it's one of the only forms of capital that is readily available.


If you’ve found this information helpful, I hope you’ll do two things for me.

1) Subscribe to this newsletter. That way, new copies are delivered directly to your inbox.

2) Share this newsletter with one other person that you think might benefit from the information I share.


By the way, I have an entire course that hundreds of startup founders have taken to help them better understand the fundraising process.

Click the button below to learn more!

Thank you for subscribing!
Please check your inbox for a link to confirm your email address.

Read past issues

May 05
This isn't 2008. But, it's not that much better
Apr 20
Market Whisperer: Knowing Your Customer Better Than Investors
Apr 14
Energized > Rested
Apr 07
Numb the pain, silence the teacher
Mar 31
The Myth of the Big Exit
Mar 23
Growth Gears: Equity vs. Debt - Fueling a Startup’s Journey
Mar 16
A candid conversation about fear
Mar 09
The Technical Product Managers Guide to Go-to-Market
Mar 03
My goal was 100 financial plans. I did 10x that goal.
Feb 25
Poor MVP, no one likes you
Feb 24
Beyond Bytes: Why Interpersonal Skills are the New Power Tools for Success
Feb 17
This one question changed how I looked at contingency plans
Feb 10
From $100k -> $75M - this week's fundraising lessons
Jan 27
The next big finance opportunity
Jan 20
This is how long a startup funding round lasts
Jan 09
How I'd market a loan broker business
Jan 02
25+ years of finance experience in less than 5 minutes
Dec 28
How to have a stress-free relationship with money
Dec 17
How to buy a business with little money down
Dec 12
Want to 10x your business? Try the strategy that most people fear.
Dec 05
Why being loan-specific as a loan broker is best
Nov 28
The Power of Micro Markets
Nov 19
Defining success criteria helps remove analysis paralysis
Nov 12
Lessons from acquisitions
Nov 07
My business plan cheat code
Oct 28
Everyone is missing the real point about being overworked
Oct 22
Why you should have a "How to work with me" manual
Oct 18
Selling eggs - my quiet ambition
Oct 13
Breaking Free from 'Meh': The Hidden Impact of a 7 Rating in Life
Sep 24
From Software Engineer to Commercial Loan Broker
Sep 23
A personal message about the importance of your health
Sep 16
Is the SBA 8(a) program going away?
Aug 21
What is a search fund?
Aug 14
My guidelines for speaking engagements
Aug 07
The Ultimate Guide to Picking the Perfect Lender for Your Business
Aug 05
Built to sell - pricing strategies that work
Jul 22
My framework for building impervious value propositions
Jul 12
How to force tradeoff decisions
Jul 09
How I'd Start a Freelance Business Today
Jul 05
The Bookends of Product Management
Jun 28
From the C-suite to Product; How I got here and what you can learn from that
Jun 17
My Digital Detox Experience
Jun 10
AI copywriters wrote this blog post
Jun 03
The SBA Just Made Business Acquisitions Easier
May 27
The power of index investing funds
May 20
The most important skill for entrepreneurs
May 06
I churned out 46,000 words in 90 days using this writing process
Apr 29
⏰ NOW is the time to turn your finance career into entrepreneurship!
Apr 22
How to build your own financial plan in under 1 hour
Apr 15
Define your audience first, then design your product
Apr 08
Getting a business loan just got harder
Mar 25
This one question is jet fuel for productivity
Mar 24
Are the rate hikes over?
Mar 18
This tool removes decision fatigue
Mar 11
The one stat keeping us out of a recession
Mar 05
One key reason raising startup funding is so hard right now
Mar 04
My framework for quickly launching profitable products
Feb 16
What’s the average business loan interest rates?
Feb 13
Everything you need to know about business loan rates
Feb 10
This one tool made me a better entrepreneur
Jan 25
This one-pager is perfect for brainstorming business ideas
Jan 18
Stop making this mistake with your startup’s target market
Jan 11
Powerful tools for researching competitors
Jan 08
User persona template demo
Jan 04
They should take my Marketing degree away
Jan 01
How to confidently charge your worth
Oct 02
Building wealth with Restricted Stock Units (RSUs)
Sep 11
What I’ve learned as a startup analyst for an angel investing syndicate
Jun 24
My favorite economic analysis tools
May 29
Which SBA Loan Has the Lowest Down Payment?
May 01
The Power of a Decision Matrix
Apr 24
Things to consider when buying a business
Apr 17
Buy a Business vs. Start One
Mar 31
How do Micro SBA Loans work?
Mar 03
Common Investor Term Sheet Components
Feb 15
3 Step Process for Generating Business Ideas
Feb 06
Thoughts on <my first Angel Investment>
Jan 11
Lessons from writing over 1,000 words per day
Jan 06
There Are Two Main Types of Business Plans
Dec 09
The Best Pitch Deck Templates