{"id":100,"date":"2026-02-03T21:34:06","date_gmt":"2026-02-03T21:34:06","guid":{"rendered":"https:\/\/www.herringbonedigital.com\/blog\/?p=100"},"modified":"2026-02-03T21:34:08","modified_gmt":"2026-02-03T21:34:08","slug":"post-14-of-24-the-top-3-seller-regrets-and-how-to-avoid-them","status":"publish","type":"post","link":"https:\/\/www.herringbonedigital.com\/blog\/2026\/02\/03\/post-14-of-24-the-top-3-seller-regrets-and-how-to-avoid-them\/","title":{"rendered":"Post #14 of 24 \u2013 The Top 3 Seller Regrets (and How to Avoid Them)"},"content":{"rendered":"\n

I\u2019ve been part of dozens of agency M&A deals \u2014 on both sides of the table.

And if there\u2019s one thing I\u2019ve learned, it\u2019s that seller\u2019s remorse is real.

Even when the money clears, even when the deal goes smoothly, many founders look back and say: \u201cI wish I\u2019d done a few things differently.\u201d

The good news? You can avoid most of those regrets \u2014 if you know what they are.

1\ufe0f\u20e3 \u201cI wish I had started preparing earlier.\u201d
Most founders underestimate how long it takes to get truly \u201csale ready.\u201d
They get that first call from a buyer, feel flattered, and think, \u201cSure, we can talk. \u201dThen they realize they don\u2019t have clean financials, their contracts are outdated, or key metrics aren\u2019t tracked.

The result? They either have to rush, or accept a lower price.

Preparation isn\u2019t just about spreadsheets \u2014 it\u2019s about telling a confident, data-backed story about your business.
Start 12\u201324 months before you think you need to. You\u2019ll thank yourself later.

2\ufe0f\u20e3 \u201cI wish I had been clearer about my role post-sale.\u201d
So many founders get to closing day without fully understanding what their life will look like after the deal.

Are you expected to stay for six months? A year? Indefinitely? Who makes decisions now?

Those details matter \u2014 a lot.

When expectations aren\u2019t aligned, frustration builds fast.
– The buyer feels like the founder is disengaged.
– The founder feels like they\u2019ve lost controly
– Clarity upfront prevents resentment later.

3\ufe0f\u20e3 \u201cI wish I had understood the deal terms better.\u201d
This one is huge. Many sellers get fixated on the top-line number and overlook the fine print.

Things like working capital adjustments, earnout conditions, and non-compete clauses can dramatically affect what you actually walk away with.

If you don\u2019t fully understand every term in your LOI or purchase agreement, ask questions. Bring in advisors who do this every day. A good lawyer or M&A advisor doesn\u2019t just protect you legally \u2014 they protect your economics and your sanity.

Selling your agency can be one of the most rewarding moments of your
career.

But it\u2019s also complex, emotional, and easy to underestimate. So be prepared and pay attention to the details

Contact us <\/a>if you\u2019re and agency owner and have considered selling or joining something bigger.<\/em><\/strong><\/p>\n","protected":false},"excerpt":{"rendered":"

I\u2019ve been part of dozens of agency M&A deals \u2014 on both sides of the table. And if there\u2019s one thing I\u2019ve learned, it\u2019s that seller\u2019s remorse is real. Even when the money clears, even when the deal goes smoothly, many founders look back and say: \u201cI wish I\u2019d done a few things differently.\u201d The […]<\/p>\n","protected":false},"author":2,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[1],"tags":[],"class_list":["post-100","post","type-post","status-publish","format-standard","hentry","category-uncategorized"],"yoast_head":"\nPost #14 of 24 \u2013 The Top 3 Seller Regrets (and How to Avoid Them) - Herringbone Digital Blog<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.herringbonedigital.com\/blog\/2026\/02\/03\/post-14-of-24-the-top-3-seller-regrets-and-how-to-avoid-them\/\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:title\" content=\"Post #14 of 24 \u2013 The Top 3 Seller Regrets (and How to Avoid Them) - Herringbone Digital Blog\" \/>\n<meta name=\"twitter:description\" content=\"I\u2019ve been part of dozens of agency M&A deals \u2014 on both sides of the table. 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