For Subscribers

More Money, More Problems: The Down Side of a Mega Valuation The bragging rights may be tempting, but achieving a jaw-dropping valuation for your company can cause problems down the line.

By Sam Hogg

Opinions expressed by Entrepreneur contributors are their own.

Entrepreneurs fight for that big first valuation just like job seekers fight for the biggest salary--figuring the more they get now, the bigger the payday will be down the road. It's inherent to the hustle. This fight over ownership and control pits entrepreneur against investor the minute talk of a company's valuation begins. The investor wants a bigger percentage of the company via a lower valuation; the entrepreneur wants the opposite. But why the hostility? The reality is that both parties could learn a bit from the smaller-piece-of-a-bigger-pie analogy. Here's why.

It's a tough way to start a wedding. Investment partnerships are pretty darn hard to break up. As such, starting your journey together after a big valuation fistfight is not wise. Investors are folks who are going to be at your side, formally and informally, for a long time. Entrepreneurs should realize that they're competing for their investors' attention and money, vying against both new opportunities and investments already in the VC's portfolio.

The last thing a founder wants is to push hard for a high valuation at the start, only to have the investors write the company off down the road because they don't have much to gain anymore.

Down rounds are bad. Too big a valuation at the starting line can set expectations too high for future rounds of capital. Unfortunately, the VC world doesn't do well with this type of correction. Going from a $10 million Series A round to an $8 million Series B round carries a stigma--namely that your team or idea was overvalued. Making matters worse, it's not the investors who usually suffer in a down round, it's the founders, who often have to give up a much larger portion of equity to secure that round and keep the lights on.

Up rounds can go only so high. Investors are always doing math, and as company valuations get increasingly high, the calculations get tougher. If the going acquisition price for a company in your industry is, say, $100 million, your investors are going to work backward from that to arrive at the maximum valuation they can stomach. If they hope to make 10 times their investment, they'll be hesitant to get involved in an initial valuation north of $10 million.

Everyone recognizes early-stage valuations as an imprecise science, but they also realize that over time, a company's value trends toward what it's actually worth. In my job as an investor, I try to set the valuation bar a little lower at the beginning and make it up to the founders in other areas: option pools, preferred returns or performance compensation, to name a few. This way everyone wins--except for maybe the founder's ego, as he or she won't get to enjoy bragging rights and buzz over a big valuation number. Instead, the founder will have to make do with a vastly improved chance for success.

Sam Hogg

Entrepreneur Contributor

Sam Hogg is a venture partner with Open Prairie Ventures, a Midwest-based venture-capital fund investing in agriculture, life-science and information technology.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Science & Technology

How I Scaled from Side Hustle to 7 Figures Using 4 AI Tools (No Tech Skills Needed)

Scale faster, work less and grow a 7-figure business — no team needed.

Buying / Investing in Business

Former Zillow Execs Target $1.3T Market

Co-ownership is creating big opportunities for entrepreneurs.

Business News

These Are the College Majors With the Lowest Unemployment Rates — and Philosophy Ranks Higher Than Computer Science

An analysis of employment data from the Federal Reserve Bank of New York shows that some humanities majors rank higher than STEM majors in employment prospects.

Money & Finance

Turn Simple Ideas Into Never-Ending Paychecks With This Low-Effort Passive Income Strategy

A micro-hustle lets you build once, sell forever and earn money while you sleep.

Money & Finance

How Much Money Do You Need to Retire Comfortably in Your State? Here's the Breakdown.

Regardless of where you spend your golden years, it pays to be realistic about the cost of living.

Business Ideas

70 Small Business Ideas to Start in 2025

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2025.