Startup CEO Reflections

A blog about building high potential businesses

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    Keep in Touch: Engaging Your Investors in Your Company’s Story

    Jen Baird / July 29, 2020

    The end of July is approaching. It is time to connect with my key investor-stakeholders on our company’s progress. This practice of routinely telling our company’s latest story is an essential component in maintaining my investors’ support.

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    Each is Unique

    January 29, 2022

    Essential Entrepreneurial Enabler: Herding Cats

    October 30, 2021

    The Importance of Framing

    May 14, 2022
  • Board of Directors,  CEO Essentials

    The Hidden Value of Board Meeting Preparation

    Jen Baird / July 25, 2020

    It is time. Time to work on the board package, again. The effort feels like an interruption to the team. So the key to maximizing the value to the startup is to recognize and leverage the hidden value of the process of Board meeting preparation.

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    Exits Are What Matters

    January 17, 2026

    Diversity in the Board Room

    November 7, 2020

    A New Era of Board Service

    June 8, 2024
  • CEO Essentials

    Your Company’s Lawyer is NOT Your Lawyer

    Jen Baird / July 22, 2020

    A few weeks ago, another CEO reached out and asked for a referral to an attorney. My first question was for the company or for yourself? I didn’t always realize that there was a difference.

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    You May Also Like

    Breakeven Point: Why It’s Not Actually a Point

    January 31, 2026

    Striving for Highest Best Use

    June 25, 2022

    Prerequisites for Synthesis

    September 18, 2021
  • Sweetspot
    Fundraising

    Too Early. Too Late. Finding the VC Fund Timing Sweet Spot.

    Jen Baird / July 18, 2020

    When raising venture capital, understand the venture fund timing sweet spot so you can align your startup’s needs with your potential investor’s needs, or at least realize when it will be hard to fit.

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    Considering Grants

    June 22, 2024

    The Challenge of Raising Money as a Solopreneur

    February 24, 2024

    Understanding the Waterfall

    October 14, 2023
  • Founding,  Fundraising

    Getting Baked for Fundraising

    Jen Baird / July 15, 2020

    Building an investable business takes more time and effort than most people realize. Too often, I see people jumping the gun and trying to fundraise too early.

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    Making a Difference

    March 2, 2024

    Considering Grants

    June 22, 2024

    Section 1202 Tax Matters

    September 23, 2023
  • Fundraising

    How VCs Say “Yes”

    Jen Baird / July 11, 2020

    When you are raising venture capital, a VC’s most common answer is ‘no.’ Sometimes, if you are lucky, they start to say ‘yes.’ Here is what that looks like.

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    Hard Fundraising Market Drivers

    September 7, 2024

    Startup Financial Modeling: Things to Know

    May 27, 2023

    The Challenge of Raising Money as a Solopreneur

    February 24, 2024
  • Fundraising

    How VCs Say “No”

    Jen Baird / July 8, 2020

    For a startup, raising venture capital is daunting. The numbers are not in your favor. Learning to recognize "no" gives you a chance to move on quickly to the next opportunity for a great fit.

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    You May Also Like

    Due Diligence Should Go Both Ways

    December 13, 2025

    Milestones

    September 16, 2023

    My Prospective VC Is Asking For Personality Tests?

    August 15, 2020
  • Permission to Innovate
    CEO Essentials,  Management

    Permission to Innovate

    Jen Baird / July 4, 2020

    Realizing the potential for process improvement requires making sure that those who are part of designing the change are empowered to find the best path.

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    CEO Whispering

    August 31, 2024

    The Value of Doing Something Intrinsically Hard

    May 29, 2021

    Advice to My Younger Self

    April 12, 2025
  • Beginning,  Founding

    How Do You Start a Company?

    Jen Baird / July 1, 2020

    It does not necessarily start with the idea since you can find a worthy idea. So how does a founding CEO actually begin?

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    Side Hustle vs. All-in

    August 5, 2023

    How and Why I Got into Startups

    May 8, 2020

    Compensating Tiny Teams

    March 3, 2023

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Startup CEO Reflections by Jen Baird 2026
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