Startup CEO Reflections

A blog about building high potential businesses

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  • Risk & Decision-Making

    Beware of AI Cons Targeting Entrepreneurs

    Jen Baird / March 7, 2026

    AI is creating a tsunami in our inboxes. As founders, entrepreneurs, and startup CEOs, we are particularly vulnerable to certain types of scams — and I have noticed a major uptick in volume over the past year or so. Let’s talk about what these new cons look like.

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    You May Also Like

    Fear of the Uncontrollable

    June 11, 2022
    Focus

    Focus Means Saying No

    September 19, 2020

    The Deep End of the Pool

    March 12, 2022
  • Board of Directors,  Liquidity Events,  Risk & Decision-Making

    Exits Are What Matters

    Jen Baird / January 17, 2026

    For founders and funders alike, exits are where value gets realized.

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

    April 30, 2022

    Getting Value from Your Board

    October 9, 2020

    Evaluating CEOs

    September 21, 2024
  • Building a Team,  Risk & Decision-Making

    Succession Planning Even in Startups

    Jen Baird / March 22, 2025

    The team is the foundation and core of a startup’s success. Yet early-stage startup teams are small and vulnerable to turnover, so proactive risk assessment and succession planning is essential for business resiliency.

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    You May Also Like

    Ask the Right Hiring Question

    March 15, 2025

    Using Retained Recruiters

    April 19, 2025

    Facilitating Team Learning Curves

    January 18, 2025
  • Building,  Management,  Risk & Decision-Making

    In-sourcing and Outsourcing

    Jen Baird / September 28, 2024

    It often seems like it would be possible to grow a startup faster by outsourcing some of the key functions to an expert service provider. Sometimes, this is true, but often, there is less leverage than you might think – and there is undoubtedly a great deal of risk.

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    You May Also Like

    You Cannot Learn All You Need to Know on the Internet

    June 17, 2023

    Every Startup is a Custom Job

    July 30, 2022

    Choices

    July 19, 2025
  • Risk & Decision-Making

    A Risk-Based Lens

    Jen Baird / July 20, 2024

    As a startup CEO, a robust risk-based lens is one of our most potent decision-making tools.

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    The Deep End of the Pool

    March 12, 2022

    Succession Planning Even in Startups

    March 22, 2025

    What is that Light?

    August 27, 2022
  • CEO Essentials,  Product Development,  Risk & Decision-Making

    Discerning Signals in the Noise

    Jen Baird / April 6, 2024

    Startup leaders must discern critical signals from noise to navigate and innovate effectively in a chaotic environment, utilizing data and customer insights.

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    You May Also Like

    The Dimension You Cannot Change

    January 8, 2022

    Fundraising is a Means

    October 28, 2023

    Building a Financial Function

    January 13, 2024
  • CEO Essentials,  Risk & Decision-Making

    Consider Your BATNA

    Jen Baird / December 2, 2023

    Deep into a critical negotiation, how far do you go? What risks do you take? How should you think about your possible positions? These are essential questions that a startup leader must navigate in myriad scenarios – and BATNA is one of the most potent tools for deciding what to do.

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    You May Also Like

    Making Luck

    October 26, 2024

    Equity Incentives for Startup Teams

    May 3, 2025

    Discerning Signals in the Noise

    April 6, 2024
  • CEO Essentials,  Risk & Decision-Making

    Making Bets

    Jen Baird / September 9, 2023

    As a startup leader forging new paths into the future, there is always uncertainty about the consequences of significant decisions. We cannot see what will happen perfectly, so we have to gather the best information available, test assumptions when possible, and ultimately pull the trigger and make a bet.

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    You May Also Like

    When Health Changes Everything

    November 15, 2025

    Legal Matters

    April 8, 2023
    Focus

    Focus Means Saying No

    September 19, 2020
  • Risk & Decision-Making

    Beyond Your Comfort Zone

    Jen Baird / March 18, 2023

    The first time you venture forth to lead in the unknown world of high-potential startups, you will definitely be moving outside your comfort zone. Fear and self-doubt are normal, despite enormous pressure to pretend you are not experiencing them.

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    And A Tree Fell Across the Path: Responding to Startup Adversity

    September 12, 2020

    Consider Your BATNA

    December 2, 2023

    Exits Are What Matters

    January 17, 2026
  • 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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    Section 1202 Tax Matters

    September 23, 2023

    CEO Whispering

    August 31, 2024

    Driving for Speed with Finesse

    March 13, 2021
  • Being a Christian CEO,  Neurosurgery,  Risk & Decision-Making

    Fear of the Uncontrollable

    Jen Baird / June 11, 2022

    As the day approached for my neurosurgery, the community of people who knew about this looming event expanded. Practically universally, when someone found out, their first response was, "that must be so scary!"

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    You May Also Like

    The Spiritual Side of My Entrepreneurial Journey

    December 26, 2020

    Appreciating Important Things in Life

    November 25, 2023

    Praying through Transitions

    December 24, 2022
  • CEO Essentials,  Management,  Risk & Decision-Making

    Building a Fireproof Team

    Jen Baird / April 23, 2022

    Building a robust and resilient team requires constant intention every step of the way so that when the going gets tough, or a crisis erupts, the fireproof team can respond. Investing to build a strong startup team that can field a startup’s inevitable curveballs is essential.

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    You May Also Like

    Milestones

    September 16, 2023

    Section 1202 Tax Matters

    September 23, 2023

    The Preeminence of the Customers’ Problem

    December 10, 2022
  • CEO Essentials,  Risk & Decision-Making

    The Deep End of the Pool

    Jen Baird / March 12, 2022

    You are often confronted with problems you haven’t solved before in a startup. Problems that no one on the team or perhaps anywhere has solved before. Being comfortable jumping into the deep end of the problem-solving pool is essential for startup success.

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    You May Also Like

    Opportunity Costs

    July 29, 2023

    Discerning Signals in the Noise

    April 6, 2024

    Clear-Eyed Optimism

    July 6, 2024
  • Risk & Decision-Making

    Are You Ready to Make the Decision?

    Jen Baird / October 2, 2021

    Leading a startup means making important decisions with incomplete information. Achieving startup success demands relentless forward motion, so when do you have enough to make a bet?

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    You May Also Like

    Making Bets

    September 9, 2023
    Focus

    Focus Means Saying No

    September 19, 2020

    The Risk of Idea Stealing

    May 15, 2021
  • Fundraising,  Product Development,  Risk & Decision-Making

    The Risk of Idea Stealing

    Jen Baird / May 15, 2021

    Inexperienced entrepreneurs often worry about sharing what they are working on with others, fearing someone will steal their idea. While there are a few circumstances one should be cautious about, generally, it is far riskier not to share.

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    You May Also Like

    Know Your Numbers

    April 20, 2024

    Milestones

    September 16, 2023

    Stock Option Grant Planning

    May 10, 2025
  • Risk & Decision-Making

    Investing in Force Multipliers

    Jen Baird / April 24, 2021

    Trading off between investing in a more systemic, force-multiplying solution versus just trying to keep up with the immediately overwhelming work at hand is difficult. Sometimes this mental image helps me recognize when I should consider stepping back and making a different choice.

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    You May Also Like

    Exits Are What Matters

    January 17, 2026

    The Risk of Idea Stealing

    May 15, 2021

    Succession Planning Even in Startups

    March 22, 2025
  • Risk & Decision-Making

    Waiting Can Be So Difficult

    Jen Baird / January 9, 2021

    As leaders, sometimes we are face situations where we must wait on third parties to act. That waiting can be hard, painful, and exhausting.

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    You May Also Like

    Investing in Force Multipliers

    April 24, 2021

    Making Bets

    September 9, 2023

    The Deep End of the Pool

    March 12, 2022
  • 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.

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    You May Also Like

    Family

    Family Enablers: The Source of an Entrepreneur’s Strength

    October 3, 2020

    Strategic Planning for Startups

    May 17, 2025
    Jen and Favory Sonata

    Prioritize Exercise While Building Your Startup

    June 20, 2020
  • Risk & Decision-Making

    And A Tree Fell Across the Path: Responding to Startup Adversity

    Jen Baird / September 12, 2020

    Unforeseen problems. Disrupted plans. Surprising changes. Startups are all about ups and downs and responding to adversity. When the unexpected occurs, it is time to swing into action.

    Read More

    You May Also Like

    Making Bets

    September 9, 2023

    In-sourcing and Outsourcing

    September 28, 2024

    Building a Fireproof Team

    April 23, 2022
  • Risk & Decision-Making

    Watch Out for Fresh, Hot Data

    Jen Baird / August 1, 2020

    As company leaders, we want to be well informed about what is happening in our startup. Yet fresh, hot data is fraught with challenges. Treat it with care.

    Read More

    You May Also Like

    Are You Ready to Make the Decision?

    October 2, 2021

    Investing in Force Multipliers

    April 24, 2021

    Fear of the Uncontrollable

    June 11, 2022

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Startup CEO Reflections by Jen Baird 2026
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