In this episode, Sasha Orloff is joined by Andrew Gazdecki, founder of Acquire.com, who shares his expertise on successfully selling companies, maximizing exit value, and key lessons from his own acquisition experiences, with over $500 million in closed deals.

 

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🙏 Help shape our show by taking our quick listener survey at https://bit.ly/TurpentinePulse.

 

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Highlights from the Episode:

• Creating a competitive process with multiple potential buyers is crucial for maximizing exit value – “if you have one buyer, you have no buyer”
• Proper preparation and documentation (clean financials, confidential information memorandum) significantly speeds up the acquisition process and builds buyer confidence
• Being transparent about business challenges upfront (“bruises and all”) builds trust and allows you to control the narrative around potential objections

 

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RECOMMENDED PODCAST:

Check out Modern Relationships, where Erik Torenberg interviews tech power couples and leading thinkers to explore how ambitious people actually make partnerships work. Founders Fund’s Delian Asparouhov and researcher Nadia Asparouhova kick off the series with an unfiltered conversation about their relationship evolution.

Apple: https://podcasts.apple.com/us/podcast/id1786227593

Spotify: https://open.spotify.com/show/5hJzs0gDg6lRT6r10mdpVg

YouTube: https://www.youtube.com/@ModernRelationshipsPod

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SPONSOR:

 

📝Notion offers powerful workflow and automation templates, perfect for streamlining processes and laying the groundwork for AI-driven automation. With Notion AI, you can search across thousands of documents from various platforms, generating highly relevant analysis and content tailored just for you – try it for free at https://www.notion.com/upstreampod

 

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LINKS:

 

Acquire: https://acquire.com/

https://www.linkedin.com/in/agazdecki/

 

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X/SOCIAL:

 

@acquiredotcom (Acquire)

@agazdecki (Andrew)

@sashaorloff (Sasha)

 

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TIMESTAMPS:

(00:00) Intro

(02:10) Personal lessons from selling Business Apps

(03:50) Building Acquire.com from personal experience

(06:49) First acquisition story with ESW Capital

(09:28) Negotiating terms and tax considerations

(12:20) Story of Altcoin acquisition

(13:53) Sponsor: Notion

(15:15) Experience at Spiff and path to Acquire.com

(18:35) Maximizing exit value strategies

(25:47) Process of listing on Acquire.com

(27:36) Types of buyers and deal sizes

(29:34) Success stories and notable deals

(32:57) Future plans for Acquire.com

(34:04) Wrap

Nico Jeannen just made a quarter-million dollar sale a couple weeks ago with the acquisition of his transcription product, Talknotes.

It’s his second sale after a string of roughly 17 startups that have seen increasing success.

Here’s how he made TalkNotes.

One day, Nico was trying to get Google to transcribe a voice note for him when he noticed the quality was poor. He crafted a prototype transcriber using an AI API and posted it on X.com (formerly Twitter) making $700 in just a few days.

He scaled further using his knowledge of SEO gained from previous projects.

Nico realized he didn’t want to spend hours fixing code and doing customer support after one round of bug fixes dipped customer acquisition by 70%. He wanted to sell quickly – before he burned out.

He listed on Acquire and secured an all-cash $200,000 deal in weeks with the help of Ebony on Acquire.com’s support team.

Listen to Andrew and Nico’s interview as they discuss:

• What Nico has learned about startups after building 17 of them
• Why Nico accepted a drastic price cut for his sale
• The dangers of playing buyers against each other

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Be sure to subscribe to see the newest acquisition stories every Tuesday and gain the knowledge to buy or sell your own online business → https://youtube.com/@acquiredotcom?sub_confirmation=1

Want more stories? Access the past 50+ acquisition stories here → https://blog.acquire.com/tag/startup-acquisition-stories-podcast/Thinking about selling your own startup? The number one question is always ‘how much can I sell for’ and we’ve got the answers in our biannual valuation multiples reports here → https://blog.acquire.com/tag/acquire-coms-acquisition-multiples-report/

Thinking about buying a startup? Sign up for a free buyer account and browse all the live listings. Upgrade only when you find the right one that fits your acquisition criteria to engage. Get Started → https://acquire.com/buyers/

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Follow the Guest: Nico Jeannen –

• https://www.linkedin.com/in/nico-jeannen/
• https://x.com/nico_jeannen

Follow the Host: Andrew Gazdecki –

• https://twitter.com/agazdecki
• https://www.linkedin.com/in/agazdecki/
• https://acquire.com

Follow Acquire.com –

• https://twitter.com/acquiredotcom
• https://www.linkedin.com/company/acquiredotcom
• https://www.tiktok.com/@acquiredotcom

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About Acquire.com:

Acquire.com is the largest and most active acquisition marketplace for buying and selling online businesses. Acquire.com is the highest rated platform for both ease and quickness to match buyers and sellers.We cater to all types of online, revenue-generating businesses while producing the highest success rates for SaaS and eCommerce/DTC businesses in the M&A industry. Join over 350,000 entrepreneurs making life-changing connections and deals everyday.

 

👉🏼 About the Guest:

Brendan Mahony is the founder of Sunset, a company that helps tech companies shut down, saving founders thousands of dollars and hundreds of hours. He is also the ex-founder of Toybox (YC S18, acquired) and Contrast (shut down). From this experience, he built Sunset!

👉🏼 About the Host:

Sharath is a founder, creator, and community builder. He is also a serial maker who built and shipped 15+ projects using no-code tools. His SaaS product Shoutout generated $30k ARR, which was sold to a UK-based product studio. Prev, Sharath worked for world-changing startups like Product Hunt and On Deck, where he helped build and nurture communities. He also grew his audience on Twitter from 200 to 24,000 using give-first principles and creating high-value content. He recently sold his second SaaS product, GuestLab, and he is working on a startup idea while hosting this show.

👉🏼 Sponsor Corner:

Shoutout to Acquire.com for sponsoring The Undefeated Underdogs podcast! They’re the best online marketplace to buy/sell startups and I know many founders who have sold their businesses there. If you’re looking to wind down your business and cash in some of your founder chips, check them out – https://try.acquire.com/sharath/

👉🏼 Description:

Listen in as Sharath and Brendan discuss raising money, finding customers at an early stage, weird startup ideas, and more!

👉🏼 Timestamps:

• 00:00: Episode Highlight
• 00:22: Shoutout to Acquire.com
• 02:47: Introduction to Brendan Mahony – founder of Sunset, a startup helping you shut down your startup correctly
• 04:33: Why create a startup about shutting down startups
• 10:00: How Brendan raised money as a first-time founder
• 19:05: How to get investors on board for your startup
• 20:50: Finding customers as an early-stage startup
• 25:20: Lessons from the first year of building Sunset
• 27:20: Building a startup at Y Combinator
• 32:34: How to bend the rules when you’re in founder mode
• 38:16: How to deal with shutting down your startup – operationally, physically, mentally, emotionally
• 42:12: What would Brendan work on if not Sunset?
• 46:00: Weird startup ideas
• 48:25: Problems startups deal with
• 50:47: Outro and closing thoughts

👉🏼 Resources:

• Link to Acquire.com: https://try.acquire.com/sharath/
• Andrew Gazdecki: https://www.andrewgazdecki.com/

👉🏼 Where to find Brendan:

• Twitter: https://x.com/bmaho2211
• Linkedin: https://www.linkedin.com/in/brendan-mahony-72929385
• Sunset: https://www.sunsethq.com/

👉🏼 Where to find Sharath:

• Twitter: https://twitter.com/5harath
• YouTube: https://www.youtube.com/@5harath
• Website: https://5harath.com/
• Newsletter: https://5harath.substack.com/
• Founder Gigs: https://foundergigs.com/