Startup CEO Reflections

A blog about building high potential businesses

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  • CEO Essentials,  Founding,  Leadership

    Entreprenurial Leadership

    Jen Baird / April 5, 2025

    Last month, Sonali and I engaged in two great conversations about entrepreneurial leadership with an emphasis on women leaders.

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    You May Also Like

    Growing into the CEO Role

    January 7, 2023

    The Cost of Context Switching

    March 27, 2021
    Family

    Family Enablers: The Source of an Entrepreneur’s Strength

    October 3, 2020
  • Beginning,  CEO Essentials,  Founding

    Are You Ready to Commit to Founding?

    Jen Baird / January 25, 2025

    Launching a startup is a big commitment in terms of time, resources, and energy. Before you leap, are you ready for that sort of commitment?

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    You May Also Like

    How and Why I Got into Startups

    May 8, 2020

    How to Get a Job as a Founding CEO

    September 26, 2020

    How Do You Start a Company?

    July 1, 2020
  • CEO Essentials,  Founding

    Breadwinner

    Jen Baird / November 2, 2024

    As an investor, I understand why angels, VCs, and even high-profile early-stage accelerators seek evidence of potential future success when evaluating newer startups. Yet would-be founders and startup fundraisers often find that one of the biggest challenges of building something new is supporting themselves and their families while doing it.

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    You May Also Like

    CEO Whispering

    August 31, 2024

    Hire When It Hurts

    February 1, 2025

    Business Founders Must Lead as Product Managers/Solution Architects

    January 11, 2025
  • Beginning,  Commercialization,  Founding

    What’s in a Name?

    Jen Baird / October 5, 2024

    Naming your high-potential startup is one of the first actions of a co-founding team. The selected name captures the essence of the fledgling company as you go out into the world raising money, connecting with partners, and ultimately selling to customers. It is a more critical and strategic decision than many realize, so let’s examine some lessons learned regarding this…

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    You May Also Like

    Beginning Again

    January 1, 2022

    Startup Genesis: Choosing a Problem to Solve

    September 5, 2020

    Side Hustle vs. All-in

    August 5, 2023
  • Founding

    Hold Out for the Right Stuff

    Jen Baird / August 10, 2024

    As a serial entrepreneur, one of the things I have learned about founding startups is the critical importance of holding out for the right idea and the right team. You will invest years of your life trying to realize the potential of your startup vision – and the idea and the team are critical success factors.

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    You May Also Like

    The Preeminence of the Customers’ Problem

    December 10, 2022
    Co-founders

    The Value of Co-Founders

    June 9, 2020

    Starting Shares

    June 15, 2024
  • Building a Team,  Founding,  Fundraising

    Talking Entrepreneurship on Invisible Ink

    Jen Baird / July 13, 2024

    Listen in to this wide-ranging discussion on many things startup! Starting, team building, fundraising, financial planning, and more.

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    You May Also Like

    Wingmen — Those Trusted to Go With You into Battle

    October 22, 2022

    Using Retained Recruiters

    April 19, 2025

    Recruiting Hearts

    January 21, 2023
  • Founding,  Fundraising

    Considering Grants

    Jen Baird / June 22, 2024

    Securing grants can aid startup funding without dilution, but involves strict restrictions, extensive effort, low success rates, and potential investor concerns.

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    You May Also Like

    How Do You Start a Company?

    July 1, 2020

    The Preeminence of the Customers’ Problem

    December 10, 2022

    Section 1202 Tax Matters

    September 23, 2023
  • Founding

    Starting Shares

    Jen Baird / June 15, 2024

    Incorporating a high-potential startup in Delaware, authorize ten million shares to avoid costly amendments, enable effective vesting schedules, and minimize franchise tax.

    Read More

    You May Also Like

    How to Get a Job as a Founding CEO

    September 26, 2020

    Talking Entrepreneurship on Invisible Ink

    July 13, 2024

    The Preeminence of the Customers’ Problem

    December 10, 2022
  • Founding,  Fundraising

    Investing in First-time vs. Serial Entrepreneurs

    Jen Baird / March 23, 2024

    First-time startup founders bring passion and unique insight, but face steep learning curves and skepticism from investors who prefer experienced CEOs for reducing investment risks.

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    You May Also Like

    How to Get a Job as a Founding CEO

    September 26, 2020

    Hold Out for the Right Stuff

    August 10, 2024

    Making a Difference

    March 2, 2024
  • CEO Essentials,  Founding

    Making a Difference

    Jen Baird / March 2, 2024

    What motivates entrepreneurs to pursue building high-potential companies? Making money? Independence? Making a difference? The answer might surprise you.

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    You May Also Like

    Armor vs. Authenticity

    March 29, 2025

    CEO = Chief Salesperson

    August 26, 2023

    Fundraising is a Means

    October 28, 2023
  • CEO Essentials,  Founding

    What Gets You Up in the Morning?

    Jen Baird / February 3, 2024

    Founding a startup to solve a problem is a big commitment.  Before you launch, you need to carefully examine your heart and motivations to ensure you are ready for the challenge of such a marathon undertaking!

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    You May Also Like

    Facilitating Team Learning Curves

    January 18, 2025

    Communicating with Investors at the Right Frequency

    May 8, 2021

    The Deep End of the Pool

    March 12, 2022
  • CEO Essentials,  Founding,  Fundraising

    Section 1202 Tax Matters

    Jen Baird / September 23, 2023

    Recently, I was reminded of the “downside” of a successful exit, specifically, that capital gains earned on investment in a startup are, generally speaking, subject to taxes. In other words, the IRS wants its piece of that nice big check. Wouldn’t it be nice if you could just keep it all instead?

    Read More

    You May Also Like

    Cap Table Housekeeping

    November 18, 2023

    Big Sticks

    July 2, 2022

    Equity Incentives for Startup Teams

    May 3, 2025
  • Beginning,  Founding,  Fundraising

    Side Hustle vs. All-in

    Jen Baird / August 5, 2023

    At the beginning of forming a startup, there is a phase where there is tension between doing the startup alongside whatever is paying the bills and committing to going all-in. Let's reflect on the factors that play into this decision.

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    You May Also Like

    Compensating Tiny Teams

    March 3, 2023

    How to Get a Job as a Founding CEO

    September 26, 2020

    Beginning Again

    January 1, 2022
  • Commercialization,  Founding,  Fundraising

    The Double-Edged Sword of Competition when Fundraising

    Jen Baird / July 15, 2023

    Sophisticated potential investors always ask about a startup’s competition. A well-developed answer is essential because “no competition” is not a good answer, and “too much competition” is also challenging.

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    You May Also Like

    The Rocket Launch Feeling

    January 22, 2022

    Careful What You Wish For

    August 3, 2024

    References and Testimonials

    May 18, 2024
  • Founding,  Fundraising,  Leadership

    Drive, Intelligence, and Integrity

    Jen Baird / June 24, 2023

    One of my favorite investors and mentors said that the essential characteristics he looks for in startup founders -- drive, intelligence, and integrity -- cannot be taught. That got me thinking about why those characteristics are essential to successful startup building and how we might recognize them. 

    Read More

    You May Also Like

    Breadwinner

    November 2, 2024

    Making a Difference

    March 2, 2024

    What Gets You Up in the Morning?

    February 3, 2024
  • Founding,  Product Development

    Keys to Customer Discovery

    Jen Baird / June 3, 2023

    When you venture forth as an entrepreneur, exploring new innovative territory that you want to build into a business, it is crucial to validate that your product concept resonates with your target customers. That is the essential function of early customer discovery.

    Read More

    You May Also Like

    Investing in First-time vs. Serial Entrepreneurs

    March 23, 2024

    Evaluating Markets Before Founding

    March 5, 2022
    Life Happens

    The Importance of Co-Founder Vesting

    June 12, 2020
  • CEO Essentials,  Founding,  Product Development

    The Preeminence of the Customers’ Problem

    Jen Baird / December 10, 2022

    Immerse yourself in your customer’s problem. The urgent and important problem IS the opportunity. Don’t build a solution looking for a problem.

    Read More

    You May Also Like

    Opportunity Costs

    July 29, 2023

    Strategic Planning for Startups

    May 17, 2025

    The Deep End of the Pool

    March 12, 2022
  • Founding,  Leadership,  Relationships

    For Me, It’s Not Just Business

    Jen Baird / October 29, 2022

    Startup CEOs come in different styles. For some, "it's just business." But, for many founder CEOs, it is far more than that as they pour all their passion into their startup and embody it profoundly. That embodied passion is often the activation energy that propels the startup out of the gate and onto a successful trajectory as it persuades others…

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    You May Also Like

    Drive, Intelligence, and Integrity

    June 24, 2023

    Starting Shares

    June 15, 2024

    Considering Grants

    June 22, 2024
  • Founding,  Product Development

    Evaluating Markets Before Founding

    Jen Baird / March 5, 2022

    Analyzing your potential market and testing concepts with potential customers are critical steps in deciding whether you have the ingredients for a potentially successful startup.

    Read More

    You May Also Like

    Drive, Intelligence, and Integrity

    June 24, 2023

    Hold Out for the Right Stuff

    August 10, 2024

    Getting Baked for Fundraising

    July 15, 2020
  • Beginning,  Founding

    How to Get a Job as a Founding CEO

    Jen Baird / September 26, 2020

    Sometimes people ask me how one gets a job as a Founding CEO. They seem to think that you update your resume and send it to someone (who?) and apply for the job.

    Read More

    You May Also Like

    Are You Ready to Commit to Founding?

    January 25, 2025

    How Do You Start a Company?

    July 1, 2020

    What’s in a Name?

    October 5, 2024
  • Beginning,  Founding

    Startup Genesis: Choosing a Problem to Solve

    Jen Baird / September 5, 2020

    Forming a startup means that the founder(s) has an opportunity to choose what problem they will invest themselves in solving. Choose wisely!

    Read More

    You May Also Like

    Compensating Tiny Teams

    March 3, 2023

    How and Why I Got into Startups

    May 8, 2020

    What’s in a Name?

    October 5, 2024
  • 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.

    Read More

    You May Also Like

    Side Hustle vs. All-in

    August 5, 2023

    Keys to Customer Discovery

    June 3, 2023

    Investing in First-time vs. Serial Entrepreneurs

    March 23, 2024
  • 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?

    Read More

    You May Also Like

    Co-Founder Dreaming

    February 25, 2023

    Side Hustle vs. All-in

    August 5, 2023

    Compensating Tiny Teams

    March 3, 2023
  • Life Happens
    Founding

    The Importance of Co-Founder Vesting

    Jen Baird / June 12, 2020

    Because life happens, co-founder vesting of equity is critical for a young high-potential startup.

    Read More

    You May Also Like

    Getting Baked for Fundraising

    July 15, 2020

    Entreprenurial Leadership

    April 5, 2025

    Starting Shares

    June 15, 2024
  • Co-founders
    Founding

    The Value of Co-Founders

    Jen Baird / June 9, 2020

    Most venture-backed companies are founded by two or more co-founders. With good reason.

    Read More

    You May Also Like

    How Do You Start a Company?

    July 1, 2020

    Evaluating Markets Before Founding

    March 5, 2022

    Startup Genesis: Choosing a Problem to Solve

    September 5, 2020
  • Delaware C-Corp
    Founding

    Start with a Delaware C-Corp If Raising VC

    Jen Baird / June 3, 2020

    When building a startup, you will face many surprising curves, so when the best path is the straight, well-traveled road, take it.

    Read More

    You May Also Like

    Making a Difference

    March 2, 2024

    The Double-Edged Sword of Competition when Fundraising

    July 15, 2023
    Life Happens

    The Importance of Co-Founder Vesting

    June 12, 2020
  • Picking a Lawyer for Your Startup
    Founding,  Fundraising

    Picking a Lawyer for Your Startup

    Jen Baird / May 20, 2020

    An expert corporate attorney is a critical asset for a high potential startup.  But what factors should you consider to find the right one?

    Read More

    You May Also Like

    Considering Grants

    June 22, 2024

    How to Get a Job as a Founding CEO

    September 26, 2020

    The Preeminence of the Customers’ Problem

    December 10, 2022

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Startup CEO Reflections by Jen Baird 2025
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