Startup CEO Reflections

A blog about building high potential businesses

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  • CEO Essentials

    Strategic Planning for Startups

    Jen Baird / May 17, 2025

    An internet search for “strategic planning” often turns up elaborate processes tailored for large organizations to tackle the problem of laying out their vision, goals, and strategies. Yet, even though having a strategic plan is essential for every organization’s success, how do we adapt these often expensive, consultant-driven processes to fit the world of a small, early-stage startup?

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    You May Also Like

    Making a Difference

    March 2, 2024

    Aligned on Success

    October 21, 2023

    Wait to Spend Until the Money is in the Bank

    October 7, 2023
  • Budgeting & Finance,  CEO Essentials,  Fundraising

    Stock Option Grant Planning

    Jen Baird / May 10, 2025

    Because the stock option pool size is a subject of fundraising negotiations, this is often the point at which the early-stage founders/CEO is first confronted with the need to develop a stock option grant plan.

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    You May Also Like

    Pricing Strategy

    November 19, 2022

    Know Your Numbers

    April 20, 2024

    Thresholds of Spending

    December 9, 2023
  • Building a Team,  CEO Essentials

    Equity Incentives for Startup Teams

    Jen Baird / May 3, 2025

    Joining a startup feels risky to many, yet the upside potential of making a difference and sharing in the financial rewards of building a success can be enticing. Startup founders and leaders should consider how to incentivize their team using equity as part of an overall compensation package.

    Read More

    You May Also Like

    Using Retained Recruiters

    April 19, 2025

    The Challenge of Raising Money as a Solopreneur

    February 24, 2024

    Facilitating Team Learning Curves

    January 18, 2025
  • Building a Team,  CEO Essentials

    Using Retained Recruiters

    Jen Baird / April 19, 2025

    Many early-stage startup leaders leverage their personal networks and use online postings to source talent. However, sometimes it makes sense to pay recruiters for help.

    Read More

    You May Also Like

    Specialties Matter

    January 28, 2023

    Equity Incentives for Startup Teams

    May 3, 2025

    Recruiting Hearts

    January 21, 2023
  • CEO Essentials

    Advice to My Younger Self

    Jen Baird / April 12, 2025

    After 35 years as a professional businessperson with almost 25 of those in the entrepreneurial ecosystem, here are the three things I have learned that I would say to my younger self.

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    You May Also Like

    Essential Entrepreneurial Enabler: Herding Cats

    October 30, 2021

    Building a Financial Function

    January 13, 2024

    Authoritative

    September 14, 2024
  • 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.

    Read More

    You May Also Like

    Hire When It Hurts

    February 1, 2025

    Pants and People

    July 9, 2022

    Communicating with Investors at the Right Frequency

    May 8, 2021
  • CEO Essentials

    Armor vs. Authenticity

    Jen Baird / March 29, 2025

    Part of leading a startup is raising money from investors, often professional investors (VCs) and high-net-worth individuals (angels). I learned over time that people who have or manage large amounts of investable capital develop “armor” to keep their distance from eager entrepreneurs. Similarly, self-taught learning to be a startup executive is often accomplished by hearing the stories of those who…

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    You May Also Like

    Facilitating Team Learning Curves

    January 18, 2025

    Not Fast Enough

    November 16, 2024

    Funding Foundations

    September 2, 2023
  • 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.

    Read More

    You May Also Like

    Consider Your BATNA

    December 2, 2023

    An Essential Entrepreneurial Enabler: Learning

    November 21, 2020

    Are You Ready to Commit to Founding?

    January 25, 2025
  • CEO Essentials,  Fundraising,  Selling

    The Power of Sales

    Jen Baird / February 15, 2025

    Founders and startup leaders, never lose sight of the power of commercial sales (a.k.a. revenue) to solve many of your problems. There are good reasons why investors are eager to jump on board a scaling commercial startup while moving cautiously on those still pre-revenue. Let’s explore why by unpacking the magic of sales.

    Read More

    You May Also Like

    Using Retained Recruiters

    April 19, 2025

    Thresholds of Spending

    December 9, 2023

    The Hidden Value of Board Meeting Preparation

    July 25, 2020
  • CEO Essentials,  Management,  Team Building

    Hire When It Hurts

    Jen Baird / February 1, 2025

    Capital efficiency is critical when relying on investor capital rather than operating income to build your company. In the early stages, hire carefully. In fact, in general, put off expanding your team prematurely by only hiring when it hurts.

    Read More

    You May Also Like

    Cap Table Housekeeping

    November 18, 2023

    Coping with Curve Balls

    June 4, 2022

    Armor vs. Authenticity

    March 29, 2025
  • 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

    Beginning Again

    January 1, 2022

    Co-Founder Dreaming

    February 25, 2023

    Compensating Tiny Teams

    March 3, 2023
  • Building a Team,  CEO Essentials,  Team Building

    Facilitating Team Learning Curves

    Jen Baird / January 18, 2025

    Leading a startup means forging new paths, building organizational infrastructure, and ultimately becoming skilled at facilitating team learning curves. This is one of the most challenging parts of being an entrepreneur trying to create a business.

    Read More

    You May Also Like

    Equity Incentives for Startup Teams

    May 3, 2025

    Using Retained Recruiters

    April 19, 2025

    Ask the Right Hiring Question

    March 15, 2025
  • CEO Essentials,  Product Development

    Business Founders Must Lead as Product Managers/Solution Architects

    Jen Baird / January 11, 2025

    The title “Solution Architect” is a specific position in the IT hierarchy of a larger organization. Yet, in the context of a smaller organization, often early-stage startup, the role of a solution architect and related product manager is often at least partially filled by the founder and startup business leader. Here are some reflections on what I have learned about…

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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

    The Dimension You Cannot Change

    January 8, 2022
  • CEO Essentials

    Not Fast Enough

    Jen Baird / November 16, 2024

    Are you feeling in control, regardless of what you show publicly? Maybe you shouldn’t because one of a startup's powerful advantages is its ability to move quickly. Yet, while essential, harnessing this advantage is challenging for entrepreneurs.

    Read More

    You May Also Like

    Big Sticks

    July 2, 2022

    Giving Thanks

    November 28, 2020

    The Magic Project Management Triangle

    January 16, 2021
  • 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.

    Read More

    You May Also Like

    Circles of Control, Influence, and Concern

    September 17, 2022

    Not Fast Enough

    November 16, 2024

    The Illusion of Control

    April 27, 2024
  • CEO Essentials

    Making Luck

    Jen Baird / October 26, 2024

    Are you lucky? Does your success flow from being in the right place at the right time? Or, when we dig beneath the surface, do we find that an entrepreneur makes their own luck? Perhaps the story of an amazingly “lucky” entrepreneur will inspire you to also create your own luck!

    Read More

    You May Also Like

    Communicating with Investors at the Right Frequency

    May 8, 2021

    Good Leaders Define Reality

    January 23, 2021

    Growing into the CEO Role

    January 7, 2023
  • CEO Essentials

    Pursuing Mythical Creatures

    Jen Baird / October 19, 2024

    The fantasy of many intrepid first-time startup entrepreneurs is to build a unicorn. Visions of technological breakthroughs, hypergrowth, and wealth creation sing a siren song as the excitement of living the dream takes hold. Yet, let us not forget that unicorns are legendary creatures rather than something you find in every woodsy glade – and there are reasons for that!

    Read More

    You May Also Like

    Reflections on Startup Children

    May 22, 2021

    Cap Table Housekeeping

    November 18, 2023

    Wait to Spend Until the Money is in the Bank

    October 7, 2023
  • CEO Essentials,  Resting

    Resilience

    Jen Baird / October 12, 2024

    Founders and startup leaders face unexpected challenges, persistent stress and uncertainty, overwhelming setbacks, and endless changes usually for years. Responding effectively and continuing to build the business demands resilience on many levels.

    Read More

    You May Also Like

    The Essential Fundraising Question: What is Your Plan?

    May 20, 2023

    What Gets You Up in the Morning?

    February 3, 2024

    The Magic of Synthesis

    September 11, 2021
  • CEO Essentials

    Authoritative

    Jen Baird / September 14, 2024

    How do we recognize leaders? Often, it is the fact that they speak authoritatively, which flows from their confidence, decision-making, and vision-casting. This matters in startups because all startup stakeholders are looking for someone who will hopefully lead an extraordinary value-creation process.

    Read More

    You May Also Like

    Facilitating Team Learning Curves

    January 18, 2025

    The Essential Fundraising Question: What is Your Plan?

    May 20, 2023

    The Dimension You Cannot Change

    January 8, 2022
  • CEO Essentials

    CEO Whispering

    Jen Baird / August 31, 2024

    The job of a startup CEO is multi-faceted and endlessly challenging. Yet, there is no degree or comprehensive playbook out there to provide the training for how to succeed. Enter the "CEO Whisperer."

    Read More

    You May Also Like

    Equity Incentives for Startup Teams

    May 3, 2025

    The Deep End of the Pool

    March 12, 2022

    Aligned on Success

    October 21, 2023
  • 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…

    Read More

    You May Also Like

    Breadwinner

    November 2, 2024

    The Essential Fundraising Question: What is Your Plan?

    May 20, 2023

    You Cannot Learn All You Need to Know on the Internet

    June 17, 2023
  • CEO Essentials

    Clear-Eyed Optimism

    Jen Baird / July 6, 2024

    A startup CEO must balance optimistic vision with realistic risk assessment, seeking advice from peers, and knowing when to pivot or stop.

    Read More

    You May Also Like

    Circles of Control, Influence, and Concern

    September 17, 2022

    Building a Financial Function

    January 13, 2024

    Are You Ready to Commit to Founding?

    January 25, 2025
  • Board of Directors,  CEO Essentials,  Relationships

    The Illusion of Control

    Jen Baird / April 27, 2024

    Owning over 51% of shares doesn't guarantee startup CEOs control due to dependence on investor funding and their significant influence.

    Read More

    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

    A New Era of Board Service

    June 8, 2024
  • Budgeting & Finance,  CEO Essentials,  Fundraising

    Know Your Numbers

    Jen Baird / April 20, 2024

    Investors prioritize startups led by individuals with strong business acumen, essential for translating technical innovation into successful, scalable businesses. Demonstrated financial management skills, including understanding financial statements and core business drivers, are crucial to gaining investor trust.

    Read More

    You May Also Like

    Cap Table Housekeeping

    November 18, 2023

    A Startup’s Chart of Accounts

    February 17, 2024

    Stock Option Grant Planning

    May 10, 2025
  • 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.

    Read More

    You May Also Like

    Opportunity Costs

    July 29, 2023

    Coping with Curve Balls

    June 4, 2022

    Delivering Sound Bites

    July 3, 2021
  • 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.

    Read More

    You May Also Like

    The Growth Moments

    September 3, 2022

    Fundraising is a Means

    October 28, 2023

    The Preeminence of the Customers’ Problem

    December 10, 2022
  • 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!

    Read More

    You May Also Like

    Not Fast Enough

    November 16, 2024

    The Dimension You Cannot Change

    January 8, 2022

    Critical Success Factor: Decision-Making

    August 24, 2024
  • Budgeting & Finance,  CEO Essentials

    Building a Financial Function

    Jen Baird / January 13, 2024

    Few startup founders come from a finance background (except perhaps fintech startups!), so building out the foundational financial function is often outside the founders’ comfort zone. Yet, building a robust financial function becomes essential as a startup grows, especially if it raises money. 

    Read More

    You May Also Like

    Pricing Strategy

    November 19, 2022

    A Startup’s Chart of Accounts

    February 17, 2024

    Thresholds of Spending

    December 9, 2023
  • Being a Christian CEO,  CEO Essentials

    Light

    Jen Baird / December 23, 2023

    I love it when someone points out yet again the difference between light and darkness. You cannot “create” darkness directly or say, “Let there be dark,” because darkness is the absence of light. To “achieve” darkness, you must remove sources of light. Any light at all diminishes darkness. On the other hand, light pours out from itself. A light source…

    Read More

    You May Also Like

    Midway through the Recovery Journey

    June 18, 2022

    Coping with Curve Balls

    June 4, 2022

    Whole Personhood

    December 30, 2023
  • Budgeting & Finance,  CEO Essentials

    Thresholds of Spending

    Jen Baird / December 9, 2023

    What seems like “a lot” of money? There is no absolute answer as it really depends on what you are used to spending routinely. This is one of those phenomena that affects entrepreneurs as they grow their companies – and it deserves some intentional management.

    Read More

    You May Also Like

    Know Your Numbers

    April 20, 2024

    Pricing Strategy

    November 19, 2022

    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.

    Read More

    You May Also Like

    Resilience

    October 12, 2024

    Milestones

    September 16, 2023

    Discerning Signals in the Noise

    April 6, 2024
  • Budgeting & Finance,  CEO Essentials,  Fundraising

    Cap Table Housekeeping

    Jen Baird / November 18, 2023

    Good housekeeping of a corporate capitalization (cap) table is an essential demonstration of a startup leader’s competence, yet it is full of potentially painful pitfalls when moving along the learning curve.

    Read More

    You May Also Like

    Pricing Strategy

    November 19, 2022

    Stock Option Grant Planning

    May 10, 2025

    Thresholds of Spending

    December 9, 2023
  • CEO Essentials,  Fundraising

    Fundraising is a Means

    Jen Baird / October 28, 2023

    Fundraising for a startup takes enormous effort over a sustained period. Companies that raise rounds issue press releases after closing. One might mistakenly begin to think that fundraising is an end instead of a means to an end.

    Read More

    You May Also Like

    Wingmen — Those Trusted to Go With You into Battle

    October 22, 2022

    The Essential Fundraising Question: What is Your Plan?

    May 20, 2023

    Investor Levers of Control

    July 8, 2023
  • Board of Directors,  CEO Essentials,  Fundraising

    Aligned on Success

    Jen Baird / October 21, 2023

    Startup fundraising is a grueling process. By the time the deal closes, a startup leader often feels embattled and exhausted, wondering if taking on investment is possibly the worst thing ever. Yet there is light after closing.

    Read More

    You May Also Like

    Investor Levers of Control

    July 8, 2023

    The Illusion of Control

    April 27, 2024
    Getting Value from Your Board

    Getting Value from Your Board of Directors

    May 30, 2020
  • CEO Essentials,  Fundraising

    Wait to Spend Until the Money is in the Bank

    Jen Baird / October 7, 2023

    When raising money or doing a big corporate deal, it pays to remember that the deal is not done until the money is in the bank.

    Read More

    You May Also Like

    The Hidden Value of Board Meeting Preparation

    July 25, 2020

    The Dimension You Cannot Change

    January 8, 2022

    Are You Ready to Commit to Founding?

    January 25, 2025
  • 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

    People Management for Startup Leaders

    February 18, 2023

    Specialties Matter

    January 28, 2023

    The Essential Fundraising Question: What is Your Plan?

    May 20, 2023
  • CEO Essentials,  Fundraising

    Milestones

    Jen Baird / September 16, 2023

    While building a startup, leaders must make critical strategic decisions about what to focus on to derisk and add value. One manifestation of this planning work is determining the key milestones that must be accomplished and the resources required to take each step. Because this is so important, it is a key focus for investors who are evaluating startup investment…

    Read More

    You May Also Like

    Reflections on Startup Children

    May 22, 2021
    Family

    Family Enablers: The Source of an Entrepreneur’s Strength

    October 3, 2020

    Making Bets

    September 9, 2023
  • 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.

    Read More

    You May Also Like

    Recognizing When You Need to Change Up Your Team

    October 31, 2020

    Clear-Eyed Optimism

    July 6, 2024

    Communicating with Investors at the Right Frequency

    May 8, 2021
  • Budgeting & Finance,  CEO Essentials,  Fundraising

    Funding Foundations

    Jen Baird / September 2, 2023

    A house built on sand is unstable, indeed. A house built on a solid foundation can support itself even when the winds howl, the rain comes, and the floodwaters rise. In business, cash is the lifeblood, and the source of that cash reveals the nature of your foundation.

    Read More

    You May Also Like

    A Startup’s Chart of Accounts

    February 17, 2024

    Startup Financial Modeling: Things to Know

    May 27, 2023

    Cap Table Housekeeping

    November 18, 2023
  • CEO Essentials,  Fundraising,  Selling

    CEO = Chief Salesperson

    Jen Baird / August 26, 2023

    Because a successful entrepreneur ultimately must build a business that profitably sells a product to meet a sufficiently sized group of customers’ unmet needs, selling is one of the keys to success.

    Read More

    You May Also Like

    The Magic of Synthesis

    September 11, 2021

    You Cannot Learn All You Need to Know on the Internet

    June 17, 2023

    The Highlight Reel Effect

    October 1, 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…

    Read More

    You May Also Like

    Funding Foundations

    September 2, 2023

    What is that Light?

    August 27, 2022

    Business Founders Must Lead as Product Managers/Solution Architects

    January 11, 2025
  • Board of Directors,  CEO Essentials,  Fundraising

    Investor Levers of Control

    Jen Baird / July 8, 2023

    Just as I was zeroing in on the closing of my first equity investment in a startup I had co-founded, my corporate attorney said, "Once this investment is closed, they can fire you." What? The investors won't own more than half of my Company. How can that be?

    Read More

    You May Also Like

    Getting Value from Your Board

    Getting Value from Your Board of Directors

    May 30, 2020

    Dysfunctional Investors Are Real

    March 8, 2025

    On the Same Side

    August 14, 2021
  • Building,  CEO Essentials

    You Cannot Learn All You Need to Know on the Internet

    Jen Baird / June 17, 2023

    The internet is a phenomenal resource, but it can be hard to figure out exactly what applies to your startup because so many variables influence how to combine elements into a cohesive solution. Remember that you cannot learn everything you need to know to build a startup online.

    Read More

    You May Also Like

    Creating, Refining, and Executing

    August 6, 2022

    Every Startup is a Custom Job

    July 30, 2022

    In-sourcing and Outsourcing

    September 28, 2024
  • CEO Essentials,  Impact

    Considering A Whole Life

    Jen Baird / June 10, 2023

    Building a startup takes an extreme level of work and commitment. Yet, there is more to life than just work. Here are some thoughts on how I have navigated this tension over twenty years.

    Read More

    You May Also Like

    Are You Ready to Commit to Founding?

    January 25, 2025

    CEO = Chief Salesperson

    August 26, 2023

    The Dimension You Cannot Change

    January 8, 2022
  • CEO Essentials,  Fundraising

    The Essential Fundraising Question: What is Your Plan?

    Jen Baird / May 20, 2023

    When introducing your startup to potential investors, there is so much to cover. Remember that the most important question to answer is what is your plan? All else is context.

    Read More

    You May Also Like

    An Essential Entrepreneurial Enabler: Learning

    November 21, 2020

    What Gets You Up in the Morning?

    February 3, 2024

    A Startup CEO Essential: Optimism

    May 21, 2022
  • CEO Essentials

    Cultivating Your Community of Champions

    Jen Baird / April 29, 2023

    As a startup founder-CEO, do not go it alone. Cultivate a community of champions who have your back and are willing to support your growth as you seek to deliver innovation and transformation.

    Read More

    You May Also Like

    Giving Thanks

    November 28, 2020

    Making Luck

    October 26, 2024

    Making a Difference

    March 2, 2024
  • CEO Essentials,  Service Providers

    Legal Matters

    Jen Baird / April 8, 2023

    As a startup founder/CEO, you quickly discover that you need to develop a working knowledge of legal contracts because there are so many contractual agreements that you need to review, and yet hiring an attorney every time you have a non-disclosure agreement or some other contract is often beyond the financial resources you have available.

    Read More

    You May Also Like

    Cultivating Your Community of Champions

    April 29, 2023

    An Ownership Mentality

    October 16, 2021

    Business Founders Must Lead as Product Managers/Solution Architects

    January 11, 2025
  • CEO Essentials

    Your Investor is Not Your Boss

    Jen Baird / March 25, 2023

    Sometimes startup leaders, especially first-time CEOs, make the mistake of thinking that their investors are their boss(es), available to help them solve their startup's problems. While experienced investors may offer some excellent value-add as they bring their distinctive point-of-view to the table, they should not be treated like a boss.

    Read More

    You May Also Like

    Building a Fireproof Team

    April 23, 2022

    The Illusion of Control

    April 27, 2024

    The Stress-Management Power of Thankfulness

    November 27, 2021
  • 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.

    Read More

    You May Also Like

    Opportunity Costs

    July 29, 2023

    Using Retained Recruiters

    April 19, 2025

    Strategic Startup Scoping

    August 20, 2022
  • Building a Team,  CEO Essentials

    Specialties Matter

    Jen Baird / January 28, 2023

    Gathering a startup team is always a challenge. Yet, nearly all startups demand assembling a diverse range of skills that will cover your bases.  This enables forward progress to the next milestone and the subsequent funding that allows you to further expand your team. Understanding the relevant specialties and sub-specialties and how to access them will often be critical to…

    Read More

    You May Also Like

    Using Retained Recruiters

    April 19, 2025

    The Challenge of Raising Money as a Solopreneur

    February 24, 2024

    Equity Incentives for Startup Teams

    May 3, 2025
  • CEO Essentials

    Growing into the CEO Role

    Jen Baird / January 7, 2023

    Every CEO that exists was once a first-time CEO, and no one offers a training class to prepare for being a startup CEO. At some level, everyone taking on the CEO mantle must learn and grow their way into fulfilling the demands of this role.

    Read More

    You May Also Like

    You Cannot Learn All You Need to Know on the Internet

    June 17, 2023

    Light

    December 23, 2023

    The Dimension You Cannot Change

    January 8, 2022
  • 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

    Using Lawyers Well

    November 14, 2020

    The Hidden Value of Board Meeting Preparation

    July 25, 2020

    Building a Fireproof Team

    April 23, 2022
  • Building a Team,  CEO Essentials

    Wingmen — Those Trusted to Go With You into Battle

    Jen Baird / October 22, 2022

    When you lead your startup into battle, you need an inner circle of wingmen (and hopefully, wingwomen) backing you up. They are the trusted few who have earned the right to fly by your side and make an impact.

    Read More

    You May Also Like

    Equity Incentives for Startup Teams

    May 3, 2025

    Specialties Matter

    January 28, 2023

    Facilitating Team Learning Curves

    January 18, 2025
  • CEO Essentials

    The Highlight Reel Effect

    Jen Baird / October 1, 2022

    When we hear stories of other startups, especially successful ones, it is easy to perceive that the path they traveled was straightforward and easy, especially if we lose sight of the highlight reel effect.   

    Read More

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    Giving Thanks

    November 28, 2020

    Clear-Eyed Optimism

    July 6, 2024

    Your Company’s Lawyer is NOT Your Lawyer

    July 22, 2020
  • CEO Essentials

    Circles of Control, Influence, and Concern

    Jen Baird / September 17, 2022

    I certainly did not invent the concept of the Circles of Control, Influence, and Concern. Still, I did learn about these ideas early in my career (I believe from Stephen Covey), and it has proved a go-to framework for thinking about the work of building a startup.

    Read More

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    Thresholds of Spending

    December 9, 2023

    Your Company’s Lawyer is NOT Your Lawyer

    July 22, 2020

    Light

    December 23, 2023
  • CEO Essentials

    The Growth Moments

    Jen Baird / September 3, 2022

    As you grow your startup, you will be confronted with moments that require fast decisions. Self-aware moments where surprise catches you off-guard, and you have to think instantaneously about what is good for the company.

    Read More

    You May Also Like

    You Cannot Learn All You Need to Know on the Internet

    June 17, 2023

    Critical Success Factor: Decision-Making

    August 24, 2024

    Keeping Eyes on Your North Star

    February 5, 2022
  • 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.

    Read More

    You May Also Like

    The Essential Fundraising Question: What is Your Plan?

    May 20, 2023

    Are You Ready to Commit to Founding?

    January 25, 2025

    An Ownership Mentality

    October 16, 2021
  • CEO Essentials

    Strategic Startup Scoping

    Jen Baird / August 20, 2022

    Recently I was chatting with a founding team who had been asked by their investor to broaden their business scope to span several vastly different industries as customer targets. Their questions reminded me of how critical and challenging it is to determine the right strategic scope for a high-potential startup.

    Read More

    You May Also Like

    The Magic of Synthesis

    September 11, 2021

    Delivering Sound Bites

    July 3, 2021

    CEO Whispering

    August 31, 2024
  • CEO Essentials,  Communication,  Relationships

    Pants and People

    Jen Baird / July 9, 2022

    Growing a high-potential business presents many opportunities and encounters with people that can be pretty intimidating. My mentor taught me that remembering the human dimension can help you engage authentically and effectively. That insight has helped me often.

    Read More

    You May Also Like

    CEO Whispering

    August 31, 2024

    Discerning Signals in the Noise

    April 6, 2024

    Delivering Sound Bites

    July 3, 2021
  • CEO Essentials,  Communication

    Big Sticks

    Jen Baird / July 2, 2022

    Organizational leaders often carry a “big stick” that sometimes puts excess weight behind any minor questions or requests they might make. This dynamic can waste a lot of organizational resources, so it is essential to be mindful when you find you have a “big stick.”

    Read More

    You May Also Like

    Pants and People

    July 9, 2022

    People Management for Startup Leaders

    February 18, 2023

    The Essential Fundraising Question: What is Your Plan?

    May 20, 2023
  • CEO Essentials,  Management

    Striving for Highest Best Use

    Jen Baird / June 25, 2022

    Resources are always limited in a startup. Applying the principle of the highest best use is a way of making more optimal choices to accomplish goals.

    Read More

    You May Also Like

    Authoritative

    September 14, 2024

    Hire When It Hurts

    February 1, 2025

    Making Bets

    September 9, 2023
  • Being a Christian CEO,  CEO Essentials,  Neurosurgery,  Resting

    Coping with Curve Balls

    Jen Baird / June 4, 2022

    Sometimes life hands you a shock – and coping with it affects everything.

    Read More

    You May Also Like

    Whole Personhood

    December 30, 2023

    Praying through Transitions

    December 24, 2022

    Appreciating Important Things in Life

    November 25, 2023
  • CEO Essentials

    A Startup CEO Essential: Optimism

    Jen Baird / May 21, 2022

    Recently I have been chatting with others in the entrepreneurial ecosystem, and we have been reflecting that, at their core, entrepreneurs must be optimists.

    Read More

    You May Also Like

    Making a Difference

    March 2, 2024

    Thresholds of Spending

    December 9, 2023

    The Magic Project Management Triangle

    January 16, 2021
  • 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.

    Read More

    You May Also Like

    The Preeminence of the Customers’ Problem

    December 10, 2022

    Milestones

    September 16, 2023

    Thresholds of Spending

    December 9, 2023
  • 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.

    Read More

    You May Also Like

    Giving Thanks

    November 28, 2020

    Keeping Promises

    July 10, 2021

    Armor vs. Authenticity

    March 29, 2025
  • CEO Essentials,  Fundraising

    I Am Not Your Friend

    Jen Baird / February 12, 2022

    Shortly after we closed our financing round, my investor sat across the table from me, drinking coffee, and declared, “I am not your friend.”  Uh, what?

    Read More

    You May Also Like

    The Dimension You Cannot Change

    January 8, 2022

    A Sense of Urgency

    October 22, 2021

    Entreprenurial Leadership

    April 5, 2025
  • 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

    Prerequisites for Synthesis

    September 18, 2021

    People Management for Startup Leaders

    February 18, 2023

    Your Investor is Not Your Boss

    March 25, 2023
  • CEO Essentials

    The Dimension You Cannot Change

    Jen Baird / January 8, 2022

    Building a startup is one giant multidimensional puzzle, but time is the one immutable dimension you cannot adjust. You can use time to your advantage in your startup, but you never lose sight of your personal need to manage your own precious time.

    Read More

    You May Also Like

    The Value of Doing Something Intrinsically Hard

    May 29, 2021

    The Highlight Reel Effect

    October 1, 2022

    Investor Levers of Control

    July 8, 2023
  • CEO Essentials,  Team Building

    Consulting as Startup Preparation Ground

    Jen Baird / December 4, 2021

    Experience as a consultant can develop useful transferrable skills for leading a high-potential startup. Yet, by itself, it is seldom enough. Here are some reflections on both sides of the coin.

    Read More

    You May Also Like

    Stock Option Grant Planning

    May 10, 2025

    Business Founders Must Lead as Product Managers/Solution Architects

    January 11, 2025

    Striving for Highest Best Use

    June 25, 2022
  • Being a Christian CEO,  CEO Essentials

    The Stress-Management Power of Thankfulness

    Jen Baird / November 27, 2021

    Every year, the Thanksgiving holiday reminds me of the stress-management power of being thankful. I suppose the challenge is continually seeking to revisit what I am grateful for all the other days of the year.

    Read More

    You May Also Like

    The Spiritual Side of My Entrepreneurial Journey

    December 26, 2020

    What We Choose to Invest Our Time In

    January 4, 2025

    Light

    December 23, 2023
  • CEO Essentials,  Communication

    Essential Entrepreneurial Enabler: Herding Cats

    Jen Baird / October 30, 2021

    Driving forward in a startup almost always comes down to herding the relevant cats into alignment to achieve the goal at hand. Herding cats requires an essential blend of skills – and the results can be quite value-creating.

    Read More

    You May Also Like

    Discerning Signals in the Noise

    April 6, 2024

    Prerequisites for Synthesis

    September 18, 2021

    An Essential Entrepreneurial Enabler: Learning

    November 21, 2020
  • CEO Essentials

    A Sense of Urgency

    Jen Baird / October 22, 2021

    Speed is a startup’s greatest advantage, therefore, startup leaders and teams must always act with a sense of urgency. This is such a comprehensive driver that I find it weaves together many of thoughts shared on this blog over the past 18 months.

    Read More

    You May Also Like

    Armor vs. Authenticity

    March 29, 2025

    Equity Incentives for Startup Teams

    May 3, 2025

    CEO = Chief Salesperson

    August 26, 2023
  • CEO Essentials

    An Ownership Mentality

    Jen Baird / October 16, 2021

    Entrepreneurs have an ownership mentality. An awareness that the buck starts and stops with them.  This truth underpins many aspects of the experience of creating a business from scratch. 

    Read More

    You May Also Like

    Investor Levers of Control

    July 8, 2023

    Business Founders Must Lead as Product Managers/Solution Architects

    January 11, 2025
    Connecting the Why

    Connecting the Why

    December 12, 2020
  • CEO Essentials

    The Value of Education

    Jen Baird / October 9, 2021

    Startup CEOs need to bring a diverse set of skills to the table, yet what is the right balance between leveraging formal education and real-world experience to build that skill set?

    Read More

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    Equity Incentives for Startup Teams

    May 3, 2025

    The Essential Fundraising Question: What is Your Plan?

    May 20, 2023

    The Power of Sales

    February 15, 2025
  • CEO Essentials

    Prerequisites for Synthesis

    Jen Baird / September 18, 2021

    Last week, I wrote about one of the essential skills for startup leaders: synthesis.  Synthesis is collecting and quickly combining ideas and parts of ideas together into a coherent whole, to provide a critically important framework of ideas that informs startup planning, decision-making, and storytelling. As I reflected further on the core enablers for effective synthesis, three essential prerequisite elements…

    Read More

    You May Also Like

    Clear-Eyed Optimism

    July 6, 2024

    The Most Important Thing

    February 6, 2021

    Advice to My Younger Self

    April 12, 2025
  • CEO Essentials

    The Magic of Synthesis

    Jen Baird / September 11, 2021

    When I think about what skills I rely on every day to build a startup, synthesis routinely tops the list.  The need to integrate many pieces of information into a coherent whole that enables you to plan, tell a compelling story, and manage risks is a never-ending need that is entirely dependent on this skill.

    Read More

    You May Also Like

    CEO Whispering

    August 31, 2024

    Stock Option Grant Planning

    May 10, 2025

    Know Your Numbers

    April 20, 2024
  • CEO Essentials

    Life’s Foundation: Health

    Jen Baird / August 28, 2021

    Building a high-potential company requires tremendous energy, focus, and stamina.  It is essential to invest in maintaining your health to sustain your ability to keep building your startup.

    Read More

    You May Also Like

    Delivering Sound Bites

    July 3, 2021

    Big Sticks

    July 2, 2022

    Authoritative

    September 14, 2024
  • CEO Essentials,  Relationships

    Keeping Promises

    Jen Baird / July 10, 2021

    Keeping promises is an expression of integrity and builds trust. This is one of the most potent principles to apply in successful startup building as well as successful life building.

    Read More

    You May Also Like

    Milestones

    September 16, 2023

    Fundraising is a Means

    October 28, 2023
    Permission to Innovate

    Permission to Innovate

    July 4, 2020
  • CEO Essentials

    Delivering Sound Bites

    Jen Baird / July 3, 2021

    Leading a startup often means being the face of and speaking for that startup. Here are a few tips and techniques gleaned over the years on how to nail interviews by delivering useful sound bites.

    Read More

    You May Also Like

    The Most Important Thing

    February 6, 2021

    Going Virtual

    June 26, 2021

    What is that Light?

    August 27, 2022
  • CEO Essentials,  Management,  Relationships

    Going Virtual

    Jen Baird / June 26, 2021

    COVID-19 hit like a freight train in the spring of 2020. We went 100% virtual in a day. And began learning and evolving our approaches to work to adapt to a new reality. Here are some initial reflections on our particular case study for the impact of the pandemic on our team.

    Read More

    You May Also Like

    The Stress-Management Power of Thankfulness

    November 27, 2021

    The Value of Education

    October 9, 2021

    Pursuing Mythical Creatures

    October 19, 2024
  • CEO Essentials

    The Value of Doing Something Intrinsically Hard

    Jen Baird / May 29, 2021

    Difficult challenges create barriers to entry, competitive advantage, and value. Seek them out.

    Read More

    You May Also Like

    What is that Light?

    August 27, 2022

    Striving for Highest Best Use

    June 25, 2022

    Essential Entrepreneurial Enabler: Herding Cats

    October 30, 2021
  • CEO Essentials

    Reflections on Startup Children

    Jen Baird / May 22, 2021

    Startups are like the children of their founders. What are the implications of this analogy?

    Read More

    You May Also Like

    Giving Thanks

    November 28, 2020

    Striving for Highest Best Use

    June 25, 2022

    Building a Financial Function

    January 13, 2024
  • CEO Essentials

    Communicating with Investors at the Right Frequency

    Jen Baird / May 8, 2021

    The more frequently you communicate, the deeper into the details you need to delve. To manage the level of detail and involvement, control the communication frequency.

    Read More

    You May Also Like

    Strategic Planning for Startups

    May 17, 2025

    The Dimension You Cannot Change

    January 8, 2022

    Life’s Foundation: Health

    August 28, 2021
  • CEO Essentials,  Management

    The Cost of Context Switching

    Jen Baird / March 27, 2021

    Leading a startup that depends on inventing new technology requires mastering the balance of context switching. Too much kills innovation. Too little means losing touch with what is essential

    Read More

    You May Also Like

    Know Your Numbers

    April 20, 2024

    Funding Foundations

    September 2, 2023

    Section 1202 Tax Matters

    September 23, 2023
  • 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

    The Illusion of Control

    April 27, 2024

    Critical Success Factor: Decision-Making

    August 24, 2024

    Keeping Eyes on Your North Star

    February 5, 2022
  • 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

    Your Company’s Lawyer is NOT Your Lawyer

    July 22, 2020
    Permission to Innovate

    Permission to Innovate

    July 4, 2020

    Big Sticks

    July 2, 2022
  • 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

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    Considering A Whole Life

    June 10, 2023

    What Gets You Up in the Morning?

    February 3, 2024

    You Cannot Learn All You Need to Know on the Internet

    June 17, 2023
  • CEO Essentials

    The Magic Project Management Triangle

    Jen Baird / January 16, 2021

    Balancing the dimensions of time, scope, and resources is a widely applicable framework for managing projects of all scales. Whatever your title, as a project manager, managing stakeholders' expectations and consistently performing successfully depends directly on your ability to set and deliver on your targets (scope) on-time (time) and on-budget (resources).

    Read More

    You May Also Like

    The Power of Professionalism

    March 1, 2025

    What Gets You Up in the Morning?

    February 3, 2024

    Business Founders Must Lead as Product Managers/Solution Architects

    January 11, 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

    The Growth Moments

    September 3, 2022

    Hire When It Hurts

    February 1, 2025

    Critical Success Factor: Decision-Making

    August 24, 2024
  • CEO Essentials

    Leadership is Lonely

    Jen Baird / December 19, 2020

    There are times along a startup CEO's journey that are profoundly lonely. It is the nature of the role.

    Read More

    You May Also Like

    I Am Not Your Friend

    February 12, 2022

    Your Company’s Lawyer is NOT Your Lawyer

    July 22, 2020

    Life’s Foundation: Health

    August 28, 2021
  • 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

    Investor Levers of Control

    July 8, 2023

    Striving for Highest Best Use

    June 25, 2022

    Cultivating Your Community of Champions

    April 29, 2023
  • CEO Essentials

    Giving Thanks

    Jen Baird / November 28, 2020

    Success as an entrepreneur depends on the contributions of many. I appreciate all the support, engagement, and encouragement over the years and ventures.

    Read More

    You May Also Like

    A Startup CEO Essential: Optimism

    May 21, 2022

    Business Founders Must Lead as Product Managers/Solution Architects

    January 11, 2025

    Equity Incentives for Startup Teams

    May 3, 2025
  • CEO Essentials

    An Essential Entrepreneurial Enabler: Learning

    Jen Baird / November 21, 2020

    Learning to learn quickly and effectively is one of the master skills of becoming a successful entrepreneur.

    Read More

    You May Also Like

    Strategic Startup Scoping

    August 20, 2022

    The Essential Fundraising Question: What is Your Plan?

    May 20, 2023

    Reflections on Startup Children

    May 22, 2021
  • CEO Essentials,  Service Providers

    Using Lawyers Well

    Jen Baird / November 14, 2020

    Lawyers can be a tremendous resource for a startup CEO, but it is essential to use them well. Knowing the role of a corporate lawyer can make all the difference.

    Read More

    You May Also Like

    Advice to My Younger Self

    April 12, 2025

    The Most Important Thing

    February 6, 2021

    The Cost of Context Switching

    March 27, 2021
  • CEO Essentials,  Team Building

    Recognizing When You Need to Change Up Your Team

    Jen Baird / October 31, 2020

    Are you unconsciously suffering from a role fit problem in your team? First recognizing and then addressing the issue is critical to startup success.

    Read More

    You May Also Like

    Discerning Signals in the Noise

    April 6, 2024

    Breadwinner

    November 2, 2024

    Considering A Whole Life

    June 10, 2023
  • Family
    CEO Essentials,  Relationships

    Family Enablers: The Source of an Entrepreneur’s Strength

    Jen Baird / October 3, 2020

    Building a company out of nothing is enormously hard work. Hidden behind most startup CEOs are tremendously supportive families. This is one of the secrets to success.

    Read More

    You May Also Like

    Leadership is Lonely

    December 19, 2020

    Keeping Eyes on Your North Star

    February 5, 2022

    Funding Foundations

    September 2, 2023
  • 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

    Giving Thanks

    November 28, 2020

    Light

    December 23, 2023

    The Hidden Value of Board Meeting Preparation

    July 25, 2020
  • 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.

    Read More

    You May Also Like

    The Illusion of Control

    April 27, 2024

    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.

    Read More

    You May Also Like

    Armor vs. Authenticity

    March 29, 2025

    Wait to Spend Until the Money is in the Bank

    October 7, 2023
    Family

    Family Enablers: The Source of an Entrepreneur’s Strength

    October 3, 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.

    Read More

    You May Also Like

    Business Founders Must Lead as Product Managers/Solution Architects

    January 11, 2025

    CEO = Chief Salesperson

    August 26, 2023

    The Highlight Reel Effect

    October 1, 2022
  • Jen and Favory Sonata
    CEO Essentials

    Prioritize Exercise While Building Your Startup

    Jen Baird / June 20, 2020

    Startups are marathons, not sprints. Figuring out how to pace yourself and your team in a healthy way has real business success consequences.

    Read More

    You May Also Like

    Coping with Curve Balls

    June 4, 2022

    Making a Difference

    March 2, 2024
    Focus

    Focus Means Saying No

    September 19, 2020

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