The Koerner Office – Ep. #238: Six Hard Lessons That Would Have Saved Me Years

Host: Chris Koerner
Date: October 24, 2025

Episode Overview

In this raw solo episode, serial entrepreneur Chris Koerner peels back the curtain on his six biggest business failures, sharing the stories, mistakes, pain, and lessons that shaped his career. Rather than boast about multi-million dollar wins, Chris gets highly personal, ranking the failures based on their emotional, mental, and career impact—not just on financial losses. This candid deep dive is intended as a reality check for fellow entrepreneurs, with the goal of saving others years of hardship by learning from Chris’s costly mistakes.

Key Discussion Points & Insights

1. The Value of Owning Your Failures

• Main Insight: Social media algorithms reward success—not failure—so authentic stories of business mistakes rarely get air time. But these stories contain the most valuable lessons.
• Quote [00:31]:

  "Entrepreneurship is anything but rainbows and butterflies. There’s a lot of hard, sucky things you gotta go through." — Chris Koerner

2. #6 — No BS Crypto: Launching in the Wrong Market

Story:

• In 2018, Chris launched a crypto project with John McAfee at the tail end of the bitcoin bubble. Despite huge community growth (70,000+), the timing was disastrous—crypto entered a harsh bear market.
• The business failed after two years, costing Chris time and energy, though he managed to avoid total financial ruin.

Lessons:

• Only start businesses where you have real control—enough equity or agency over key decisions.
• Don’t tie yourself to markets you can’t influence (“swimming upstream during a bust is impossible”).

Quote [02:58]:

"Making a crypto business work in that market is like a goldfish trying to swim up Niagara Falls."

Memorable Moment:

• Chris is grateful he didn’t do an ICO, avoiding more severe fallout for investors.
• Despite the failure, the experience boosted his confidence:

  "...learning that I’m capable of doing cool things like that." [05:18]

3. #5 — Phone Restore: A Partnership Gone Wrong

Story:

• Chris had four iPhone repair stores, then merged with competitors he hardly knew—despite plenty of “yellow flags.”
• The deal, poorly structured and rushed, left Chris with diluted shares (down from 33% to 16% without consent) and no “mailbox money” as promised.

Lessons:

• Never partner in haste; vet partners thoroughly.
• Maintain transparency and legal clarity—know what you’re signing.
• Don’t hand over control without oversight.
• Sometimes, business success still feels like personal failure if handled poorly.

Quote [09:26]:

"I literally handed over the keys to my business without any visibility into the bank accounts…and they took advantage of that."

Memorable Moment:

• News of dilution landed while Chris was in China, 2AM—a gutting moment of helplessness.
• Despite eventually clawing back equity through “an idiot lawyer” and cashing out, Chris laments the personal and emotional price.

4. #4 — Send Eats: Letting Toxic Clients Poison the Business

Story:

• The company—a 3PL e-commerce fulfillment provider—grew to $400K/mo but hemorrhaged money, with 90% of revenue tied to one abusive client.
• Chris faced a breaking point while at his daughter’s hospital bedside, culminating in firing the customer (and thus, most staff).

Lessons:

• Fire toxic clients early, even at financial risk.
• Be relentless about financial metrics and real profitability, not just top-line growth.
• Protect your mental health.

Quote [11:45]:
(Excerpt from the October 21, 2021 Email)

“You are volatile, hostile, and unpredictable to work with…there is a direct correlation between the strength of our working relationship with your company and your involvement therein.”

Memorable Moment [12:33]:

• Chris reads from the actual "breakup" email with the client.

“We are happy to continue working with you if you are not involved in the communication between us.”

5. #3 — Backstabbed by Partners: Losing Out on $50 Million

Story:

• Built a company with two partners, received a $50M investment offer.
• The partners (one a close family friend) conspired to cut Chris out, close the company, and reopen without him, slashing his stake from 33% to 3%.

Lessons:

• Know your partners deeply; trust, but verify.
• Protect yourself legally in structuring equity and control.
• Even devastating failures can birth new opportunities. Afterward, Chris began creating content, ultimately leading to millions of monthly views.

Quote [14:36]:

“I know it sucks, I know it’s wrong, but you’re out. I’m doing this anyway. I know it’s wrong. I’m doing this anyway."
— Partner during their falling-out

Big Idea:

“…any bad thing in life that happens to us…given enough time, that bad thing will turn into a good thing.”
[16:43]

6. #2 — Bitcoin Mining: Betting the Farm at the Worst Time

Story:

• In 2021, as China banned bitcoin mining, Chris and his partner bought a mining facility, thinking it was the “perfect storm” for US miners.
• At first, it worked: $10M in 90 days, but the market quickly turned—difficulty soared, bitcoin price dropped, investors and customers lost money, including Chris and his family.

Lessons:

• Markets can turn on a dime—don’t bet big without the ability to adapt.
• Heavy external dependencies create existential risk.
• Don’t sell high-risk investments to friends/family.

Quote [19:22]:

“Mining became very, very profitable. Basically you could spend, like, $500 in electricity to mine a $5,000 bitcoin…I’m oversimplifying, but it was like—stupid.”

Memorable Moment:

• Chris reflects on the emotional cost as friends who bought in lose money:

  “I was eating my own dog food...but most of our customers lost money.” [22:24]

7. #1 — Losing a Best Friend Over Business: The iPhone Parts Company

Story:

• Founded a wholesale iPhone parts company, brought in best friend as partner.
• Grew fast, but Chris’s distracted leadership, industry commoditization, and poor stewardship led to financial losses and a painful falling out.
• Ultimately, the personal relationship didn’t survive.

Lessons:

• Regrets can be useful drivers for growth:
• Don’t confuse business growth with sustainable leadership.
• Partnerships with friends come with immense risk—more complex than marriage in some ways.

Quote [26:27]:

“If we truly don’t have regrets, then what are we really improving towards? I think it’s good to have regrets because regrets drive us to be better.”

Memorable Closing Thought [28:21]:

“A business partnership is more difficult than a marriage…There’s no stigma attached to partnering with someone too quickly in business, but there should be.”

Major Takeaways and Closing Reflections

• The Pattern: Chris’s biggest mistakes consistently stemmed from poor partnerships—whether due to lack of due diligence, unclear roles, or misplaced trust.

• Business Partnerships:

  • 50/50 rarely works unless both partners are equally invested, side by side.
  • Prefer unequal splits that recognize true engagement and accountability.

• Enduring Principle:

  “Given enough time, any failure can become a win—but only if you keep moving, learning, and striving to be better.” [16:55]

Notable Quotes (with Timestamps)

• "Entrepreneurship is anything but rainbows and butterflies." — Chris Koerner [00:31]
• “Making a crypto business work in that market is like a goldfish trying to swim up Niagara Falls.” [02:58]
• “I literally handed over the keys to my business without any visibility into the bank accounts…and they took advantage of that.” [09:26]
• "You are volatile, hostile, and unpredictable to work with…” (from the ‘breakup’ email) [11:45]
• “I know it sucks, I know it’s wrong, but you’re out. I’m doing this anyway.” — Former Partner [14:36]
• “Given enough time, that bad thing will turn into a good thing.” [16:43]
• “Mining became very, very profitable…It was like—stupid.” [19:22]
• “If we truly don’t have regrets, then what are we really improving towards?” [26:27]
• “A business partnership is more difficult than a marriage...” [28:21]

Useful Timestamps

• 00:00 — Chris’s introduction & the motivation behind discussing failures
• 01:25 — The problem with discussing failures publicly
• 02:00–05:45 — No BS Crypto failure story & lessons (#6)
• 05:46–10:41 — Phone Restore merger disaster and partnership lessons (#5)
• 10:42–13:20 — Send Eats, toxic client story and the power of firing customers (#4)
• 13:21–16:50 — Partners betrayal, losing a $50M deal, and finding purpose after loss (#3)
• 16:51–25:00 — Bitcoin mining, market risk & managing losses (#2)
• 25:01–End — iPhone parts company: friendship, regrets, and partnership wisdom (#1)

Final Thoughts

This episode delivers a rare, unfiltered look at the messy side of entrepreneurship, emphasizing hard-won wisdom you won’t find in Instagram highlight reels. Chris’s humility, candor, and actionable advice offer significant value to founders, side hustlers, and anyone interested in building — and sustaining — successful ventures.

“High risk, high reward. But, man, watch out. Be careful. Know what you’re getting yourself into.”
— Chris Koerner [29:38]