Lessons From Talking With Investors

Lessons From Talking With Investors

This is is part of my live-learning series! I will be updating this post as I continue through my journey. I apologize for any grammatical errors or incoherent thoughts. This is a practice to help me share things that are valuable without falling apart from the pressure of perfection. 

Speak Ai’s First Investment Round

These insights are coming from my journey as an entrepreneur. Recently, we shared that we want to do our first round of investment for Speak Ai.

We’ve bootstrapped to date and this was a difficult decision but ultimately one that is crucial for our continued growth. 

Why Raise Now?

We are seeing consistent growth in the number of sign-ups and application usage. We see strong patterns in the reasons people are signing up to use the platform. We are getting repeated requests to add functionality to our system that we can’t with our current capacity. 

How To Do Cold Investor Outreach

Some of the investor conversations that I have had have come completely from cold outreaches. This is a challenge and art on its own. As I’ve gone through this process, I’ve learned a few interesting things.

Be Concise

I’m an over communicator by nature. My emails are long. I talk too much. So, when I send emails, I need to restrain myself from over-explaining and adding too much information. 

One Call-to-Action

This comes from marketing and sales in general. The more choices or calls-to-action you have, the less likely your primary call-to-action will work.

Other Lessons From Talking With Investors

People Who Said They Would Invest Don’t

This has been really interesting. When starting the process and sharing that we were going to do our first round of funding at Speak Ai, I had many interested parties who had followed us for a long time said they would contribute. 

However, when asked to contribute to the round, you start to get different responses. A few of the main responses I’ve heard to date are that they want to see the terms from a lead investor, that they want access to the data room, that they are not personally investing right now, and straight-up nos.

You Have Constant Conflict Between Sales And Fundraising

This part I don’t enjoy. I’m still involved in a lot of the sales, marketing and product development in the company. So, when I am talking with investors, I am learning a lot, but part of our business is suffering. I hope to be able to hire and delegate tasks better, but our team has reached full capacity and it’s a hard thing to do.  

Recommendations For You

If you are raising funding, based on my own research and experience going through the process to date, here are some recommendations I’d like to make.

Keep Your Story Simple

This is a tough one for us. We’ve built complex technology. We have lots of use cases in. By the time we share the details of our platform, use cases, and problems that we are solving, we have fired off so much information the mental paradigm for what we are doing can start to be unclear. 

Over and over again we are given feedback we need to focus on one specific customer, use case and that our business is unclear. 

Secure Your Lead Investor Before Announcing Round

Once you have a lead investor, a lot of other things get easier. 

Put a Defined Timeline In Place

Raising investment is time-intensive and mentally testing. You want to get back to selling and growing the business, but you are constantly having conversations, seeking new investors to connect with, updating your deck and responses to questions and being told no for a multitude of reasons. 

If you make no timeline, this could drag on for too long and have a detrimental impact on your growth. 

Have Your Data Room Ready

You don’t know when your conversations will progress and all a sudden an investor is asking about your Cap Table and data room and more. If you don’t have that ready, you seem unprofessional and unprepared. 

Good Updates Are Important

One of the items that we have continuously heard great feedback on has been our quarterly updates. We put a lot of work into producing those and ensuring they are high-quality. 

As we seek investment, we are starting to do monthly updates. With all updates, you should be focusing on revenue growth, signups and software usage.


How To Send The Perfect Cold Email To An Investor | by Bill Wilson | The Startup | Medium
How to write an email to an investor | Ideas by We
5 Questions To Ask Yourself Before Sending Any Email
3 Questions to Ask Yourself Before Pitching an Investor

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