Head-On Strategies

02/21/2026

Toxic leaders pose significant risk--and are a huge liability--to your organization. I'm not sure how many CEOs realize this. A repost...

SNL Evil Boss courtesy of SNL and NBC

07/14/2025

🎉 Recharged after the Nasdaq Milestone Momentum Summit here in Chicago!

🎤 Keynote address • Panels & founder chats • Interactive time capsule 🎗️ Alumni pinning, oath + scarf • Evening networking vibes

Feeling energized, inspired, and ready to bring this momentum into my strategic projects.

Were you there? What moment resonated most for you?

05/12/2025

How Tariffs Are Crushing Small Businesses: ‘Nobody in Power Seems to Care’

Owners are laying off staff and tapping personal savings, hoping to hold out until a trade deal with China; an $8,752 fee on a $5,649 orderThe owner of a San Francisco card-game company cashed in his money-market funds. The founder of a tent maker is …

05/10/2025

We celebrate small businesses everyday but HAPPY SMALL BUSINESS SATURDAY!

03/20/2025

New Blog from Head-On Strategies! "How Small Business Owners Can Navigate Major Challenges in 2025"

Running a small business has never been easy but in 2025, the new administration brings new challenges that require strategic planning, financial resilience, and adaptability. From rising costs to changing regulations, small business owners must stay ahead of the curve to thrive. Here are the biggest concerns for entrepreneurs this year, and how to tackle them head on.

Read more and join the conversation here.

Running a small business has never been easy but in 2025, the new administration brings new challenges that require strategic planning, financial resilience, and adaptability. From rising costs to changing regulations, small business owners must stay ahead of the curve to thrive. Here are the bigges

03/17/2025

The fight is now. The CDFI Fund is under attack. If this stands, small businesses, homeowners, and entire communities will be cut off from the capital they need to survive and thrive. We cannot let that happen.   The March 14th executive order threatens to dismantle one of the most powerful tools ...

03/17/2025

Nonprofits may have reason to be optimistic about fundraising this year, but it is likely going to depend on the economy.

Of people who plan to give in 2025, 79% expect to give the same or more. This is the highest percentage since 2021.

See more trends about individual donors: https://blog.candid.org/post/5-takeaways-planned-charitable-giving-individual-donors/

03/12/2025

New Blog from Head-On Strategies! Strengthening Nonprofits for the Future: Overcoming Key Risks and Building Long-Term Sustainability

The nonprofit sector faces increased financial, regulatory, and operational challenges but with the right strategies, organizations can build resilience and long-term sustainability.

In our latest blog, we explore key risks nonprofits must navigate over the next several years and offer practical solutions to strengthen financial health, compliance, and cybersecurity while maintaining mission impact.

Read more and join the conversation here.

Nonprofits are entering a period of heightened financial, operational, and regulatory risk due to shifting policies, economic uncertainty, and evolving donor expectations. The current administration's executive actions, particularly those affecting federal funding, diversity initiatives, and social

03/12/2025

New blog post from Head-On Strategies: "The Future of Higher Education"

The Future of Higher Education

02/02/2025

We're celebrating our past, present, and future today and every day.

Happy Black History Month 2025!!!

01/22/2025

The National Council of Nonprofits has published a useful resource, "Executive Orders That Will Impact Charitable Nonprofits," that analyzes orders signed this week.

Since his inauguration, President Trump has signed dozens of executive orders covering a broad range of issues, including many that impact charitable nonprofits directly or indirectly. Some won’t take effect immediately and will be challenged in court.

Check out our analysis of how the executive orders may impact diversity, equity, and inclusion programs; government grants and contracts; civic engagement; immigration; and certain nonprofit subsectors: https://bit.ly/4jslYIM

We will be updating this document as more executive orders are announced.