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

    Keeping Eyes on Your North Star

    February 5, 2022

    The Power of Sales

    February 15, 2025

    Pants and People

    July 9, 2022
  • CEO Essentials,  Fundraising,  Leadership

    The Power of Professionalism

    Jen Baird / March 1, 2025

    Investors excited about funding high-potential startups are also eager to mitigate their risk by ensuring that the startup founders and leaders are experts in their domain with the professional expertise to build a high-growth company. That often unspoken reality puts a premium on startup leaders' reputations for professionalism.

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    You May Also Like

    Legal Matters

    April 8, 2023

    Going Virtual

    June 26, 2021

    Prerequisites for Synthesis

    September 18, 2021
  • Being a Christian CEO,  Impact,  Leadership

    What We Choose to Invest Our Time In

    Jen Baird / January 4, 2025

    Each of us must find our own source of motivation – and what works for me may not work for you. However, let me encourage you to take a few moments to reflect and consider what we each are doing and why as we enter a new year. To be mindful and intentional about what matters to us.

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    You May Also Like

    Fear of the Uncontrollable

    June 11, 2022

    Light

    December 23, 2023

    When Health Changes Everything

    November 15, 2025
  • Leadership

    Leadership Lessons from an African Village Headman

    Jen Baird / November 23, 2024

    When I think of southern Africa, I do not necessarily assume that there are leadership lessons that would be relevant to my U.S.-based entrepreneurial ecosystem. A close encounter and extended conversation with an African Village Headman showed me the brilliance of the solutions they are devising.

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    You May Also Like

    Celebrate!

    December 18, 2021

    Play Strengths, Not Weaknesses

    February 20, 2021

    Drive, Intelligence, and Integrity

    June 24, 2023
  • Leadership

    Balancing Macro and Micro Elements

    Jen Baird / November 9, 2024

    Successfully leading a startup involves paying attention to both the macro trends that define your field of play as well as the micro-actions required to successfully overcome the challenges before you. To succeed, startup leaders must be able to zoom in and out adroitly to keep both the big, out-of-your-control factors in mind, while focusing on those micro elements and…

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    You May Also Like

    Evaluating CEOs

    September 21, 2024

    It Takes a Village to Build a Startup

    November 26, 2022

    The Why Behind

    December 16, 2023
  • Board of Directors,  Leadership

    Evaluating CEOs

    Jen Baird / September 21, 2024

    Evaluating employee performance has a certain framework, however, that framework is applied somewhat differently when assessing a startup CEO. A CEO is ultimately responsible for an organization's performance, so the core of a CEO evaluation is fundamentally an organizational evaluation.

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    You May Also Like

    Board of Directors – Good News + Bad News

    July 1, 2023

    A New Era of Board Service

    June 8, 2024

    The Illusion of Control

    April 27, 2024
  • CEO Essentials,  Leadership

    Critical Success Factor: Decision-Making

    Jen Baird / August 24, 2024

    Startup leaders, especially CEOs, must be effective decision-makers because a huge portion of the job of leading a startup is making an avalanche of decisions in many domains and often with limited context. Decision-making is a skill that can be developed. Yet it also demands the confidence to decide even when context and information are limited. If you are not…

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    You May Also Like

    Investor Levers of Control

    July 8, 2023

    Prerequisites for Synthesis

    September 18, 2021

    The Hidden Value of Board Meeting Preparation

    July 25, 2020
  • Leadership

    Unintentional Blocking

    Jen Baird / July 27, 2024

    Leadership means empowering teams, not freezing them.

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    You May Also Like

    Opportunity Costs

    July 29, 2023

    Leadership Lessons from an African Village Headman

    November 23, 2024

    The Shift from Hiring Generalists to Hiring Specialists in a Startup

    August 22, 2020
  • Board of Directors,  Fundraising,  Leadership

    Looking through the Keyhole

    Jen Baird / March 30, 2024

    Investors and Board members can't fully understand a startup's intricate operations, akin to viewing through a keyhole. They should focus on crucial aspects rather than all details.

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    You May Also Like

    Investors Who Survey the Landscape While Protecting the Focus of Their Startup Teams

    April 30, 2022

    Evaluating CEOs

    September 21, 2024

    The Hidden Value of Board Meeting Preparation

    July 25, 2020
  • Communication,  Leadership

    The Why Behind

    Jen Baird / December 16, 2023

    Getting everyone aligned and moving in the same direction is a critical startup leader responsibility and skill. Articulating the “why” behind the direction makes all the difference by supplying the underlying reasons, motivations, or rationales behind a particular direction, decision, proposal, or action.

    Read More

    You May Also Like

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

    July 29, 2020

    The Three Strikes Communication Rule

    May 6, 2023

    Pants and People

    July 9, 2022
  • CEO Essentials,  Leadership

    Opportunity Costs

    Jen Baird / July 29, 2023

    The founding CEO of a startup always has more to do than they can fit into their available time – even if they are working every waking hour (which I do not recommend, by the way). That means one of the most significant success factors for such CEOs is their ability to consider opportunity costs and make wise decisions about…

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    You May Also Like

    Building a Financial Function

    January 13, 2024

    The Growth Moments

    September 3, 2022

    Thresholds of Spending

    December 9, 2023
  • 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. 

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    You May Also Like

    How Do You Start a Company?

    July 1, 2020

    Keys to Customer Discovery

    June 3, 2023

    Side Hustle vs. All-in

    August 5, 2023
  • CEO Essentials,  Leadership

    People Management for Startup Leaders

    Jen Baird / February 18, 2023

    One of the greatest challenges of founding and growing a startup company is learning to manage a team of people to accomplish amazing things on a shoestring as fast as possible.

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    You May Also Like

    Discerning Signals in the Noise

    April 6, 2024
    Jen and Favory Sonata

    Prioritize Exercise While Building Your Startup

    June 20, 2020

    I Am Not Your Friend

    February 12, 2022
  • Leadership,  Management

    The Value of Being Decisive

    Jen Baird / February 11, 2023

    Being able to decide without all of the information you might wish for is a critical startup leadership skill. Often, a clear direction to move drives more value creation than taking time and resources to achieve an incrementally better decision.

    Read More

    You May Also Like

    It Takes a Village to Build a Startup

    November 26, 2022

    What We Choose to Invest Our Time In

    January 4, 2025

    Executive Mindset

    February 26, 2022
  • Leadership,  Team Building

    It Takes a Village to Build a Startup

    Jen Baird / November 26, 2022

    A village combines the contributions of many people to build a functioning community, which is an excellent metaphor for what it takes to build a successful startup. And this Thanksgiving season, I am reflecting on how thankful I am for those who have joined the villages I have been part of.

    Read More

    You May Also Like

    What is that Light?

    August 27, 2022

    For Me, It’s Not Just Business

    October 29, 2022

    The Why Behind

    December 16, 2023
  • 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

    Startup Genesis: Choosing a Problem to Solve

    September 5, 2020

    Breadwinner

    November 2, 2024

    Are You Ready to Commit to Founding?

    January 25, 2025
  • CEO Essentials,  Leadership,  Risk & Decision-Making

    What is that Light?

    Jen Baird / August 27, 2022

    There are moments when you are not sure if what you see is a light at the end of a tunnel or an oncoming train.

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    You May Also Like

    The Key to Ongoing Leadership = Trustworthy Execution

    May 30, 2026

    Making a Difference

    March 2, 2024

    Coping with Curve Balls

    June 4, 2022
  • Leadership

    The Definition of a Leader

    Jen Baird / March 19, 2022

    Leaders come in all shapes, sizes, colors, and styles. Some are more effective than others, but in its most fundamental form, the definition of a leader is someone who can attract followers.

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    You May Also Like

    The Most Important Thing

    February 6, 2021

    The Power of Professionalism

    March 1, 2025

    Executive Mindset

    February 26, 2022
  • Leadership,  Team Building

    Executive Mindset

    Jen Baird / February 26, 2022

    An executive mindset does not depend on the job title but on the ability to synthesize, direct, and know when to enforce and when to break the rules.

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    You May Also Like

    Evaluating CEOs

    September 21, 2024

    People Management for Startup Leaders

    February 18, 2023

    Focus. Execute. Panic is Unhelpful.

    January 2, 2021
  • CEO Essentials,  Leadership

    Keeping Eyes on Your North Star

    Jen Baird / February 5, 2022

    Finding the right north star for your startup's stage of development is a powerful focusing tool to maximize your progress.

    Read More

    You May Also Like

    Breadwinner

    November 2, 2024

    I Am Not Your Friend

    February 12, 2022

    The Key to Ongoing Leadership = Trustworthy Execution

    May 30, 2026
  • Leadership

    Celebrate!

    Jen Baird / December 18, 2021

    Building a startup can be a long slog. Look for the moments to celebrate. For your and everyone else’s sake.

    Read More

    You May Also Like

    Play Strengths, Not Weaknesses

    February 20, 2021

    What is that Light?

    August 27, 2022

    Critical Success Factor: Decision-Making

    August 24, 2024
  • Leadership,  Team Building

    Intentionally Empowering Each Other

    Jen Baird / March 20, 2021

    One of the great aspects of being part of a high-performing team is how each member of the team intentionally contributes to empowering each other, which elevates both our collective process and our combined results.

    Read More

    You May Also Like

    Play Strengths, Not Weaknesses

    February 20, 2021

    The Power of Professionalism

    March 1, 2025

    Looking through the Keyhole

    March 30, 2024
  • CEO Essentials,  Leadership

    Driving for Speed with Finesse

    Jen Baird / March 13, 2021

    Speed is one of the great advantages of small, talented, focused startup teams – and the driver of the racing startup vehicle is the CEO. Yet like racing, it is essential to drive with finesse to maximize speed while not spinning out of control.

    Read More

    You May Also Like

    Giving Thanks

    November 28, 2020

    Specialties Matter

    January 28, 2023

    Consider Your BATNA

    December 2, 2023
  • Leadership,  Management

    Play Strengths, Not Weaknesses

    Jen Baird / February 20, 2021

    Our impulse is that we should improve upon our weaknesses, whether they are yours or your teammates. Sometimes our impulses are wrong.

    Read More

    You May Also Like

    Connecting the Why

    Connecting the Why

    December 12, 2020

    Celebrate!

    December 18, 2021

    Entreprenurial Leadership

    April 5, 2025
  • Leadership,  Team Building

    Catch Them Being Good

    Jen Baird / February 13, 2021

    Carrots and honey beat sticks and vinegar every time. When leading a team, pay attention so you can catch them being good.

    Read More

    You May Also Like

    Entreprenurial Leadership

    April 5, 2025

    People Management for Startup Leaders

    February 18, 2023

    Unintentional Blocking

    July 27, 2024
  • CEO Essentials,  Impact,  Leadership

    The Most Important Thing

    Jen Baird / February 6, 2021

    Successful startups focus on the most important thing: building a real and successful business.

    Read More

    You May Also Like

    CEO = Chief Salesperson

    August 26, 2023

    What is that Light?

    August 27, 2022

    The Power of Professionalism

    March 1, 2025
  • CEO Essentials,  Leadership

    Good Leaders Define Reality

    Jen Baird / January 23, 2021

    One of the critical roles of an effective leader is to define reality for the group they are leading. In doing so, they cast a vision for the future direction of the organization.

    Read More

    You May Also Like

    Not Fast Enough

    November 16, 2024
    Focus

    Focus Means Saying No

    September 19, 2020

    Hire When It Hurts

    February 1, 2025
  • CEO Essentials,  Leadership

    Focus. Execute. Panic is Unhelpful.

    Jen Baird / January 2, 2021

    The ability to control your reactions and execute under pressure is essential to successfully leading a startup.

    Read More

    You May Also Like

    Pursuing Mythical Creatures

    October 19, 2024

    Making a Difference

    March 2, 2024

    Wingmen — Those Trusted to Go With You into Battle

    October 22, 2022
  • Connecting the Why
    CEO Essentials,  Leadership

    Connecting the Why

    Jen Baird / December 12, 2020

    The most potent guiding star in sales, decision-making, and leadership is knowing, connecting, and communicating the why.

    Read More

    You May Also Like

    Family

    Family Enablers: The Source of an Entrepreneur’s Strength

    October 3, 2020

    Stock Option Grant Planning

    May 10, 2025

    Prerequisites for Synthesis

    September 18, 2021
  • Focus
    CEO Essentials,  Leadership,  Risk & Decision-Making

    Focus Means Saying No

    Jen Baird / September 19, 2020

    Everyone knows that maintaining focus is essential to startup success, yet distractions are both tempting and endless. A vital tool for the startup leader’s toolbox is the ability to say no.

    Read More

    You May Also Like

    Aligned on Success

    October 21, 2023

    The Hidden Costs of Founding

    July 5, 2025

    Going Virtual

    June 26, 2021
  • Leadership,  Team Building

    The Shift from Hiring Generalists to Hiring Specialists in a Startup

    Jen Baird / August 22, 2020

    At inception, the founding team of a startup must be small, but mighty. As the company grows, a shift occurs as the team reaches critical mass, and it becomes feasible to start hiring specialists. Recognizing this new stage of growth is essential.

    Read More

    You May Also Like

    Balancing Macro and Micro Elements

    November 9, 2024
    Connecting the Why

    Connecting the Why

    December 12, 2020

    Critical Success Factor: Decision-Making

    August 24, 2024
  • Mindsets
    Leadership,  Team Building

    For Today’s Startup Problem-Solving, Are We Cooking or Baking?

    Jen Baird / August 5, 2020

    The work of building a startup varies. Sometimes it is more like cooking. Sometimes it is more like baking. Pick the right skill set for the job at hand.

    Read More

    You May Also Like

    What is that Light?

    August 27, 2022

    Focus. Execute. Panic is Unhelpful.

    January 2, 2021

    The Most Important Thing

    February 6, 2021

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Startup CEO Reflections by Jen Baird 2026
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