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May 9, 2023 · 46m · founders-journal

Is it Time To Pivot ‘The Plunge’?

Jesse Pujji · 23m spoken Alex Lieberman · 18m spoken
0:00 / 0:00

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Co-hosts Alex Lieberman and Jesse Pujji analyze the operational, psychological, and financial hurdles of early-stage entrepreneurship, debating product iterations for 'The Plunge' and scaling strategies for Alex's executive ghostwriting agency. Through personal war stories, they provide actionable frameworks on capital allocation, workplace culture, energy management, and effective leader-team communication.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Alex holds 44.5% of the talking time here. How this is scored →

Alex as informed peer 5.3 Guest teaching 5.8 Guest disagreement 3.5 Alex pushing back 2.8
05100:0015:0030:0045:004:10–8:53 · Alex as informed peer 6/10 Unspoken Founder Realities and Diversity as Good Business Alex and Jesse have a highly collaborative discussion on founder realities and DEI as a smart business strategy. Alex brings specific details from Morning Brew's scaling days, while Jesse expands on the commercial value of diverse representation.8:54–18:22 · Alex as informed peer 4/10 Debating the Future and Product Iteration of The Plunge Jesse directly challenges Alex's plan to pivot The Plunge, pointing out that Alex is reacting prematurely to initial resistance and fear of losing money. Alex admits his anxiety around upfront capital and receptive to Jesse's critique.18:22–24:05 · Alex as informed peer 5/10 Founder Risk Profiles and Capital Allocation Strategies Jesse coaches Alex on overcoming piecemeal funding anxieties by setting aside a single tranche of risk capital upfront. Alex reflects openly on his bootstrapper mindset and aversion to capital loss.24:05–33:28 · Alex as informed peer 6/10 Blueprint for Scaling Alex's Executive Content Agency Alex presents his executive ghostwriting agency unit economics, but Jesse schools him on prioritizing an operator/CEO and building franchise playbooks rather than obsessing over supply bottlenecks alone.33:32–42:05 · Alex as informed peer 6/10 Navigating Founder Sacrifice, Intuition, and Energy Audits Jesse and Alex engage in mutual self-reflection about founder identity, Enneagram profiles, and energy audits. Both share personal frameworks with mutual validation and zero hostility.42:06–45:53 · Alex as informed peer 5/10 Listener AMA: Delivering Hard Feedback to Defensive Bosses Both hosts answer a listener inquiry regarding managing up to defensive founders. Jesse emphasizes asking permission and understanding founder pressure, while Alex brings in Radical Candor principles.4:10–8:53 · Guest teaching 3/10 Unspoken Founder Realities and Diversity as Good Business Alex and Jesse have a highly collaborative discussion on founder realities and DEI as a smart business strategy. Alex brings specific details from Morning Brew's scaling days, while Jesse expands on the commercial value of diverse representation.8:54–18:22 · Guest teaching 8/10 Debating the Future and Product Iteration of The Plunge Jesse directly challenges Alex's plan to pivot The Plunge, pointing out that Alex is reacting prematurely to initial resistance and fear of losing money. Alex admits his anxiety around upfront capital and receptive to Jesse's critique.18:22–24:05 · Guest teaching 7/10 Founder Risk Profiles and Capital Allocation Strategies Jesse coaches Alex on overcoming piecemeal funding anxieties by setting aside a single tranche of risk capital upfront. Alex reflects openly on his bootstrapper mindset and aversion to capital loss.24:05–33:28 · Guest teaching 8/10 Blueprint for Scaling Alex's Executive Content Agency Alex presents his executive ghostwriting agency unit economics, but Jesse schools him on prioritizing an operator/CEO and building franchise playbooks rather than obsessing over supply bottlenecks alone.33:32–42:05 · Guest teaching 5/10 Navigating Founder Sacrifice, Intuition, and Energy Audits Jesse and Alex engage in mutual self-reflection about founder identity, Enneagram profiles, and energy audits. Both share personal frameworks with mutual validation and zero hostility.42:06–45:53 · Guest teaching 4/10 Listener AMA: Delivering Hard Feedback to Defensive Bosses Both hosts answer a listener inquiry regarding managing up to defensive founders. Jesse emphasizes asking permission and understanding founder pressure, while Alex brings in Radical Candor principles.4:10–8:53 · Guest disagreement 2/10 Unspoken Founder Realities and Diversity as Good Business Alex and Jesse have a highly collaborative discussion on founder realities and DEI as a smart business strategy. Alex brings specific details from Morning Brew's scaling days, while Jesse expands on the commercial value of diverse representation.8:54–18:22 · Guest disagreement 6/10 Debating the Future and Product Iteration of The Plunge Jesse directly challenges Alex's plan to pivot The Plunge, pointing out that Alex is reacting prematurely to initial resistance and fear of losing money. Alex admits his anxiety around upfront capital and receptive to Jesse's critique.18:22–24:05 · Guest disagreement 4/10 Founder Risk Profiles and Capital Allocation Strategies Jesse coaches Alex on overcoming piecemeal funding anxieties by setting aside a single tranche of risk capital upfront. Alex reflects openly on his bootstrapper mindset and aversion to capital loss.24:05–33:28 · Guest disagreement 4/10 Blueprint for Scaling Alex's Executive Content Agency Alex presents his executive ghostwriting agency unit economics, but Jesse schools him on prioritizing an operator/CEO and building franchise playbooks rather than obsessing over supply bottlenecks alone.33:32–42:05 · Guest disagreement 2/10 Navigating Founder Sacrifice, Intuition, and Energy Audits Jesse and Alex engage in mutual self-reflection about founder identity, Enneagram profiles, and energy audits. Both share personal frameworks with mutual validation and zero hostility.42:06–45:53 · Guest disagreement 3/10 Listener AMA: Delivering Hard Feedback to Defensive Bosses Both hosts answer a listener inquiry regarding managing up to defensive founders. Jesse emphasizes asking permission and understanding founder pressure, while Alex brings in Radical Candor principles.4:10–8:53 · Alex pushing back 2/10 Unspoken Founder Realities and Diversity as Good Business Alex and Jesse have a highly collaborative discussion on founder realities and DEI as a smart business strategy. Alex brings specific details from Morning Brew's scaling days, while Jesse expands on the commercial value of diverse representation.8:54–18:22 · Alex pushing back 4/10 Debating the Future and Product Iteration of The Plunge Jesse directly challenges Alex's plan to pivot The Plunge, pointing out that Alex is reacting prematurely to initial resistance and fear of losing money. Alex admits his anxiety around upfront capital and receptive to Jesse's critique.18:22–24:05 · Alex pushing back 3/10 Founder Risk Profiles and Capital Allocation Strategies Jesse coaches Alex on overcoming piecemeal funding anxieties by setting aside a single tranche of risk capital upfront. Alex reflects openly on his bootstrapper mindset and aversion to capital loss.24:05–33:28 · Alex pushing back 3/10 Blueprint for Scaling Alex's Executive Content Agency Alex presents his executive ghostwriting agency unit economics, but Jesse schools him on prioritizing an operator/CEO and building franchise playbooks rather than obsessing over supply bottlenecks alone.33:32–42:05 · Alex pushing back 2/10 Navigating Founder Sacrifice, Intuition, and Energy Audits Jesse and Alex engage in mutual self-reflection about founder identity, Enneagram profiles, and energy audits. Both share personal frameworks with mutual validation and zero hostility.42:06–45:53 · Alex pushing back 3/10 Listener AMA: Delivering Hard Feedback to Defensive Bosses Both hosts answer a listener inquiry regarding managing up to defensive founders. Jesse emphasizes asking permission and understanding founder pressure, while Alex brings in Radical Candor principles.

speaking balance: gold is Alex, purple is the guest (3 minute bins)

0:00 · Alex 52.7% · guest 47.3%0:00 · Alex 52.7% · guest 47.3%3:00 · Alex 45% · guest 55%3:00 · Alex 45% · guest 55%6:00 · Alex 25.9% · guest 74.1%6:00 · Alex 25.9% · guest 74.1%9:00 · Alex 75.2% · guest 24.8%9:00 · Alex 75.2% · guest 24.8%12:00 · Alex 56.5% · guest 43.5%12:00 · Alex 56.5% · guest 43.5%15:00 · Alex 29.5% · guest 70.5%15:00 · Alex 29.5% · guest 70.5%18:00 · Alex 65.6% · guest 34.4%18:00 · Alex 65.6% · guest 34.4%21:00 · Alex 25.9% · guest 74.1%21:00 · Alex 25.9% · guest 74.1%24:00 · Alex 91.6% · guest 8.4%24:00 · Alex 91.6% · guest 8.4%27:00 · Alex 13% · guest 87%27:00 · Alex 13% · guest 87%30:00 · Alex 3.9% · guest 96.1%30:00 · Alex 3.9% · guest 96.1%33:00 · Alex 36.6% · guest 63.4%33:00 · Alex 36.6% · guest 63.4%36:00 · Alex 35.4% · guest 64.6%36:00 · Alex 35.4% · guest 64.6%39:00 · Alex 60.2% · guest 39.8%39:00 · Alex 60.2% · guest 39.8%42:00 · Alex 37.1% · guest 62.9%42:00 · Alex 37.1% · guest 62.9%45:00 · Alex 79.9% · guest 20.1%45:00 · Alex 79.9% · guest 20.1%
Sharpest disagreement ▶ 13:06 Jesse challenges Alex's pivot rationale

Jesse candidly rejects Alex's justification for pivoting The Plunge, telling him he simply forgot how hard early-stage building is and is overreacting.

 Hardest push from Alex ▶ 21:05 Alex explains fear of hiring expensive CEO upfront

Alex pushes back on Jesse's prompt to hire a CEO immediately, defending his hesitation with the very real risk of paying a $150k salary before having steady cash flow.

 Biggest teaching moment ▶ 16:45 Jesse reframes risk capital allocation

Jesse educates Alex on why writing piecemeal checks creates an emotional tax, advising him to commit a single lump sum and accept the loss upfront.

 Alex holds their own ▶ 24:05 Alex details content agency unit economics

Alex breaks down the financial math of his ghostwriting venture, demonstrating strong domain grasp of pricing, margins, and target client volume.
the scores for every segment, with the reasoning behind each
ChapterTopicAlex as informed peerGuest teachingGuest disagreementAlex pushing backWhy
Unspoken Founder Realities and Diversity as Good Business 6322 Alex and Jesse have a highly collaborative discussion on founder realities and DEI as a smart business strategy. Alex brings specific details from Morning Brew's scaling days, while Jesse expands on the commercial value of diverse representation.
Debating the Future and Product Iteration of The Plunge 4864 Jesse directly challenges Alex's plan to pivot The Plunge, pointing out that Alex is reacting prematurely to initial resistance and fear of losing money. Alex admits his anxiety around upfront capital and receptive to Jesse's critique.
Founder Risk Profiles and Capital Allocation Strategies 5743 Jesse coaches Alex on overcoming piecemeal funding anxieties by setting aside a single tranche of risk capital upfront. Alex reflects openly on his bootstrapper mindset and aversion to capital loss.
Blueprint for Scaling Alex's Executive Content Agency 6843 Alex presents his executive ghostwriting agency unit economics, but Jesse schools him on prioritizing an operator/CEO and building franchise playbooks rather than obsessing over supply bottlenecks alone.
Navigating Founder Sacrifice, Intuition, and Energy Audits 6522 Jesse and Alex engage in mutual self-reflection about founder identity, Enneagram profiles, and energy audits. Both share personal frameworks with mutual validation and zero hostility.
Listener AMA: Delivering Hard Feedback to Defensive Bosses 5433 Both hosts answer a listener inquiry regarding managing up to defensive founders. Jesse emphasizes asking permission and understanding founder pressure, while Alex brings in Radical Candor principles.

Statements from this episode (10)

Assertion Supported
Pujji: Most DTC e-commerce buyers are women
“The funny thing about Ampush in particular was most of the people who click and buy e-commerce direct to consumer things are women.”
Jesse Pujji May 9, 2023 ▶ 8:06
Disclosure
Lieberman spent $36k developing The Plunge with zero revenue so far
“Like, I've spent 36,000 dollars on this game. My guess is to truly take it to market. If we run the, we're working with the Kickstarter agency, we run like their paid ad plan that they want to run with us. It's probably gonna be another 20 K. That's 56,000 dol…”
Alex Lieberman May 9, 2023 ▶ 16:10
Disclosure
Lieberman expects his content agency to command 50% margins on $10k retainers
“On the other hand, I have this content agency where I have a high degree of confidence that I can charge clients six to 10,000 dollars per month and make a 50% margin on that, and I'm like, that feels really nice.”
Alex Lieberman May 9, 2023 ▶ 16:31
Prediction Not checkable as stated
Pujji: The Plunge could be a $10M business generating $2M annual profit
“Cause I think it, I still believe what I've said to you every time, which is, is this going to be a hundred million dollar business? I don't know, but do I think it could be a ten million dollar business that made one to two million dollars a year? A hundred p…”
Jesse Pujji May 9, 2023 ▶ 17:53
Insight
Pujji: Internal company initiatives often yield higher returns than outside investments
“Inside of a company, oftentimes the returns on capital are way higher than even an investor ever gets. Like there's initiatives, hiring five salespeople can have a 500% return in a year if you do it well, right?”
Jesse Pujji May 9, 2023 ▶ 21:32
Insight
Pujji: Generating $1M SaaS ARR is as hard as $1M services EBITDA
“Getting a million dollar SaaS ARR is probably as hard as getting a million dollars in EBITDA, let's say in a services business. And guess what? They value those streams are valued exactly the same. So like the market is very efficient in terms of how it treats…”
Jesse Pujji May 9, 2023 ▶ 23:50
Insight
Pujji: Agency founders must exit service delivery to scale successfully
“You and the CEO have to be out of the delivery of the service other than maybe coming in, whatever you're willing to do once a week, once a month. With like, I'll review stuff and give specific comments. And that's, and when you do that, it all gets up leveled…”
Jesse Pujji May 9, 2023 ▶ 31:37
Disclosure
Pujji continued running Ampush for years solely to satisfy external expectations
“And I know for many, many years at ampush, that was like the only reason I was continuing to run the company. And it took me multiple years to like unwind that from myself.”
Jesse Pujji May 9, 2023 ▶ 35:12
Insight
Pujji: Founders react defensively because they lack internal psychological safety
“Consider for a second that that founder doesn't know how to create safe space for themselves. How about that? Right. They have no idea how to actually even not judge and criticize themselves, much less anybody else.”
Jesse Pujji May 9, 2023 ▶ 44:04
Insight
Lieberman: Radical Candor applies in reverse when delivering feedback upward
“I also think it's kind of like in some ways the reverse of radical candor from Kim Scott, which like I generally view that as you as a manager, what's the best way to land feedback with your employee. But I think it works in the reverse where it's like give yo…”
Alex Lieberman May 9, 2023 ▶ 45:09
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