In the latest episode of *How to Unf**k Your Startup*, I sat down with Andrew Dumont, a startup veteran whose entrepreneurial journey began at the tender age of 18 when he cofounded Tatango, a group text messaging startup that raised an angel round and set the stage for his future endeavors. Since then, he has been a driving force behind numerous successful startups, wearing many hats along the way.

From his time as a key player at betaworks, a startup studio that has invested in household names like Tumblr, Medium, and Kickstarter, to his role as CMO at Bitly, where he built and led the revenue and gotomarket teams, Andrew has demonstrated a knack for building and scaling companies. Recently, he served as the CEO of Stamped, a SaaS company in the ecommerce space, and also led multiple brands under the umbrella of Tiny, a publiclytraded holding company. Now, as the founder and CEO of Curious, an investment firm and holding company, Andrew is on a mission to help other entrepreneurs navigate building their startups.

Andrew shared his unique perspective on the venture capital landscape, exploring the hidden pitfalls that can accompany venture funding, the importance of aligning founder and investor incentives, and the mental and emotional toll that the constant pressure to scale rapidly can take on both founders and their teams. But perhaps most importantly, our conversation also shed light on the oftenoverlooked alternatives to the traditional venture capital path. From bootstrapping to revenuebased financing, we delved into the strategies and approaches that can help founders maintain control over their vision, build resilient and profitable businesses, and ultimately achieve their goals on their own terms.

Whether you're a firsttime founder just starting out or a seasoned entrepreneur looking to get in the game once again, this episode will give you a lot to chew on.

Here are the four points that stuck with me after our conversation:

The Pitfalls of Misaligned Incentives (09:26)
The Fatigue of Constant Pivots (09:58)
Bootstrapping for Autonomy and Success (34:10)
Exploring Alternative Financing Options After Bootstrapping (35:08)