Blog Friday Q&A

Friday Q & A: Quitting Your Job to Pursue a Startup, Doing Influencer Outreach in a Massive Market, and Raising Cash in the Early Days of a Business

wrote this on

Every Friday, we’re answering your questions about business, startups, customer success and more.

Happy Friday!

In our new Groove Friday Q & A segment, we’re answering any questions that you have about, well, anything.

A huge thank you to SS, Gaurav Gulati and Joshua S. for this week’s questions.

Check out this week’s answers below, and jump in with your own thoughts in the comments!

Should I quit my job to pursue my startup idea?

This is an issue that a lot of future entrepreneurs grapple with.

It’s a tough one, and a deeply personal one.

Without knowing details about your business, your job, your personal life and your finances, I can’t really give you an answer.

But in every in-depth conversation I’ve had with people considering quitting their job, the wisest decision is "no" as often as it’s “yes.” And if you’re just now beginning to consider the prospect, it may be too early.

It comes down to thinking very carefully about why you’re thinking of quitting your job, and considering the other options.

Quitting your job is a hugely drastic move. So, why do you think it’ll help?

If it’s because you think you need more time…well, are you spending every waking minute outside of your job working on your business? And if not, try that first and see what that does to your growth.

Think hard about your motivation, and see if there’s another way to accomplish your "next step" goal while staying in your job.

Despite the glorification of going all in, keeping your business as a side project until it’s validated and has some traction can be a smart move in many cases.

Are you prepared, financially and mentally, to work for 6 months (or more) without any income?

If you have a spouse or significant other, are they prepared for that, too?

Are you okay with the possibility of being back to square one in 6 or 12 months, except without the security of a job?

I like to mitigate risk as much as possible, and there’s a lot of risk involved in jumping ship this early on in your startup journey.

I’d put in every hour that you can getting your company off of the ground, doing customer development and building your prototype.

But unless you can justify the leap without hesitation… until you can’t RESIST the leap… I’d likely do it on the side. For now.

Is influencer outreach harder in a massive market?

I don’t see a huge playing field as a disadvantage. I see it as an opportunity.

In a small market where influencers are easy to find, everyone is trying to court those influencers. This results in influencers having far more inbound requests than they can manage, and many people—even those doing influencer outreach "right"—being told no.

A huge playing field, on the other hand, is a huge opportunity.

First of all, it’s a lot easier to find influencers that closely relate to your specific segment of the market, simply by picking posts that your audience has shared and using the BuzzSumo strategy from this post.

All you need to do is:

  1. Find a few pieces of content that have been successful in your space.
  2. Enter the URL in BuzzSumo’s search field.
  3. Click on “View Sharers”

You’ll get a list of influencers that shared content that’s similar to yours:

Which makes for a terrific place to start your influencer outreach.

Second, you don’t need to engage with every influencer in your market.

You can get meaningful results early on simply by engaging with five. And then ten. And then 20.

My advice is to not be daunted by a big playing field. See it for the opportunity that it is. Many are struggling with the opposite problem and have to crawl around the internet on their hands and knees looking for a single influencer that matches their market.

The grass is always greener, I suppose :)

Do you wish you raised more money in the early days of Groove?

There are things I would’ve done differently (and I’ve blogged about many of them), but raising more money isn’t one of them.

There are so many dangers to raising cash that early that I’ve seen materialize among friends and peers.

One of the biggest is that there’s a really good chance that, like many startups, you may have to pivot to reach product/market fit.

The investors who buy into your vision today might not love the thought of your new direction. A lot of people who think they want to invest in startups don’t truly have the stomach for what being involved in a startup really means, and they end up getting scared and becoming a distraction (or worse) for the founder.

Dilution, too, is a very real de-motivator of founders and teams. You’re going to be paying a premium for capital when you’re still in the idea (or even prototype) phase, vs. when you already have traction/customers and can get far more favorable terms.

It depends on your goals, too.

For me, I wanted to build a sustainable long-term business rather than a rapid ramp to acquisition.

Going slow in the beginning and spending a ton of time talking to customers and refining the vision and product ended up being an invaluable investment in the long run.

Send me weekly updates about Groove’s Friday Q&A

Thank you for subscribing!

Your Turn: Ask Groove Anything

I’d love for this new weekly segment to be successful, and provide a valuable repository of answers from our entire community for entrepreneurs everywhere.

To do that, I need your help.

Here’s what you can do to get involved:

  1. Ask questions. Post them in the comments of this post, or Tweet them to us at @Groove.
  2. Answer questions. Every Friday, we’ll post a new Q&A segment. If you have anything to add or share regarding any of the questions asked, jump in! Many of you are far more qualified than I to speak on some of the topics that people ask me about.
1,483 Shares
← Older Post Newer Post →

From “aha” to “oh shit”, we’re sharing everything on our journey to $10M in annual revenue. We’re learning a lot and so will you.

About the Author

Alex Turnbull is the CEO & Founder of Groove (simple helpdesk software for small businesses) who loves to build startups and surf.

You might also like: