How to not waste 6 months figuring out sales

Title: How to not waste 6 months figuring out sales

Read time: 4 min

Today, I want to talk about something I see frequently in the startup business. It's about isolation, accountability, and why a lot of founders wait way too long to ask for help.

I've been connected to many teams over the last 8 years, and there's one pattern that shows up over and over that honestly breaks my heart.

Founders grinding alone. Burning through leads. Losing deals they should've closed. All because they think asking for help means they've failed.

Earlier this week, I hopped on a Zoom call with a founder I'd talked to a little over 4 months ago. Within the first 30 seconds, I could see his body language and tone just deflate.

"I f***ed up," he said. "I thought I could figure this out on my own."

Four months of grinding. Burning leads. Ghosting deals. His two co-founders were asking questions he didn't have answers for. Their runway was getting tight, and he shared a little about his mental health that I won’t share here.

We talked for an hour and twenty minutes. By the end, I think I helped. I just listened and gave him my honest advice.

This isn't a one-off. It's a pattern I see play out constantly.

Trying to build a company and have it succeed is like eating glass while staring into the abyss.

~Elon Musk

I speak to so many founders come to me after they've already been struggling for months. Sometimes a year, and they always say some version of the same thing: "I knew I needed help. I just thought I should be able to figure this out myself."

When you're a founder, admitting you don't know what you're doing feels like admitting you're a fraud. You raised money from smart people. Your team is counting on you. Your family thinks you've got this figured out.

So you tell yourself you just need a little more time. A few more reps. Scroll through bookface a little more trying to find sales nuggets.

Meanwhile, you're dying inside.

What actually changes when you stop going at it alone

A very successful YC founder came to me three months ago. She had built and sold her previous company for a lot of money. All the growth of that company was through PLG (product led growth). She though that running a sales led motion would be very similar. Not really. She hadn't closed a deal in two months. Thought her product was the problem.

I listened to one of her calls.

"You're letting them off the hook, and you have no structure" I told her. "You're asking great questions, but once they give you a weak answer, you fold. You're not pushing."

She didn't even realize she was doing it.

Three and half weeks later, she closed her biggest deal to date. Not because her product changed. Because she stopped letting prospects bullshit her.

That's the stuff you can't see when you're stuck in your own head.

Another founder was spending 90% of his time perfecting his pitch deck. Pipeline empty, but he kept telling himself once the deck was perfect, everything would click.

"Your deck isn't the problem," I told him. "You have nobody to pitch it to. We need to fix your outbound."

He didn't want to hear it. But once we got him actually talking to people, ugly deck and all, deals started moving.

Sometimes you just need someone to tell you the truth you don't want to hear.

The lonely part nobody talks about

This job has shown me how lonely being a founder really is. I talked about this last week.

Your friends don't get it. Your family thinks you're crazy. Your co-founder is dealing with the same shit you are, so you can't really lean on them, and you sure as hell can't post on LinkedIn: "I'm scared I'm not good enough for this."

So you just carry it, alone. Until you can't anymore.

I think the reason I have really good relationships with my clients long after we work together is because I'm not here to judge them. I've seen every version of stuck. The technical founder who can't bring themselves to pick up the phone. The ex McKinsey guy who's great at frameworks but can't close a deal. The repeat founder who crushed it last time but this market's different.

None of them are broken. They're just stuck in patterns they can't see.

Here’s what you can do this week

1. Record and review three sales calls

Listen for these specific patterns:

• Talk time ratio: Are you talking more than 30%? You're talking too much.

• Pushback moments: When they give you a vague answer like "we're handling it internally," do you just move on? Or do you dig in with "Help me understand, if it's handled, what prompted you to take this call?"

Write down the exact moment where each deal died. That's your pattern.

2. Build a "patterns I can't see" doc

Three columns: What I did | What happened | What I should've done instead

Do this for your last 5 deals that ghosted. Then show it to someone, another founder, a mentor, someone who knows sales. Ask them: "What am I missing here?"

3. Role-play one objection every morning for 5 minutes

Pick the objection that kills your deals most often. Set a timer. Say your rebuttal out loud. Record it on your phone.

Do this every morning before your first call for two weeks. Your confidence will completely change.

4. Ask one person for help this week

Not "eventually." This week.

Send them this: "Hey, I'm stuck on (specific problem). I've been trying to figure it out for [timeframe] and it's not working. Would you be open to a 20-minute call to tell me what I'm missing?"

Most people who've been there will say yes. You just have to ask.

Takeaway

I can't make you reach out. Some founders will read this, nod along, and then go back to grinding alone for another three months.

If you're tired of feeling stuck, tired of burning leads, tired of lying awake wondering if you're cut out for this, then let's talk.

Book a call. I'll listen to where you're at. I'll tell you what I see, and we'll figure out if working together makes sense.

Or just hit reply and tell me what's going on. I read and respond to every message.

Let's get you moving again. 💪

See you all next week!

Darren

P.S. If you’re a venture-backed company interested in coaching, book a call here.