Episode 27: How to juggle your main hustle and side hustle

I recently chatted with an early-stage founder about how she balances her relationship, her full-time gig (sales) and her side hustle (the startup). She shared that she and her partner work on the side hustle together, but it becomes hard to turn off work because they live together and work together.

We also talked about the challenges of scaling the company - specifically when it made sense to transition from looking for generalists to specialists. We talked about marketing to business development to monetization.

Here are the main takeaways from our conversation:

Leverage experts (for free initially)

The challenge is that by the time you reach the expertise level needed to be a specialist, your time is spare, and therefore, you require a high price tag (exceptions can be made, but generally, experts aren’t looking to do free work).

Instead of cold messaging a bunch of people asking for ‘quick chat’ or ‘coffee to pick your brain’, my recommendation is to take a first pass at doing the thing and then go ask an expert for feedback on how you can improve for the next time.

If you are doing a product launch for the first time, do your best job documenting and then reach out to a product marketer and ask for feedback. Do your first press release and then reach out to someone in public relations. Make your first financial model and then reach out to someone in pricing for feedback.

When you reach out and ask for feedback from an expert, you have made the ask clear and specific about why you need their help, reducing the risk that you will waste their time. If they truly are an expert, it will likely only take them a few minutes to suggest 2-3 things that will 10x your outcomes next time.

Here’s a template you can use (almost verbatim what was sent to me):

I often get generic ‘can we chat’ notes, but the above note clearly articulated what they need and where I can be helpful. Since I was traveling, they ended up putting the questions in a Google Doc, and in 2 minutes, I found 3 changes that helped them identify willingness to pay and avoid paying an agency to do this work for them.

Leverage paid pilots

In the beginning stages, you will be experimenting with the right offering, personas, and ways to monetize. While experimentation is a good thing, you can very quickly become overcommitted without the right resourcing to deliver.

One recommendation is to use paid pilots to mitigate risk on your side. If you are going to build out something brand new that is bespoke to a specific client (initially) then ask for this to be a paid pilot program.

You outline the deliverables, timeline, ownership, and success criteria (i.e., how do we know we are done) and, in exchange, ask for a set amount. For example if you are delivering training materials for a corporation over the next 2 months, make this a $20,000 deliverable after which you can re-evaluate with your main point of contact if it makes sense to continue.

Once you have refined the scope of work and price point for the first client, you can work on figuring out how repeatable this offering is for other clients. Start with your first client and ask for introductions to their counterparts at other organizations. People often know the folks in their field, especially at a similar scale, and once you’ve completed work, you can use them as a reference.

While you may not have the recurring revenue figured out, these short-term paid pilots allow you to continue experimenting and delivering on big commitments by bringing contractors or software to help.

Leverage personalized incentives & rewards

People have different career goals at different stages of their careers. If they are trying to break into a role, then having a title/specific scope of work is the priority. If they are mid-career then reaching a specific title (Director, VP, etc.) is an important milestone. For others title is irrelevant as long as they feel compensation is in the right ballpark.

As companies evolve, they need different types of people, and as people evolve, their needs evolve as well. Taking the time to identify and understand the incentives of the early contributors individually is key. If someone values flexibility, then have them start on a project-by-project work as a contractor. If someone wants that first big title allow them to build out a team.

This consistent reflection — what would excite me to be here every day — starts with the founders. You can only divide so much work by background, and eventually, you will get to a bucket of work that no one knows how to do, and one person probably wants to learn less.

Check-in with yourself often and build a regimen of reflection - at minimum quarterly and ideally monthly - to ensure that you consistently have the right people working on the things that excite them the most and that their impact on the business will be maximized. If it’s their first time leading a team, but they want the title, they are self-incentivized to figure it out for their own self-satisfaction at the very least.

Rewarding employees for meeting/exceeding these goals is also very important and has to be tailor-made to each employee. For example, I’ve always had a goal to hit ‘Director’ in title by age 30. Working backwards, that meant 1-2 years I needed to be at Sr. Manager, 3-4 years before I needed to be at Manager level. Career paths aren’t always linear (for example if I pivoted into a different role this would likely require a lateral move or a step down) but title was the key debate.

For one of my good friends, internal acknowledgment was the primary motivator for her to do better work. When our manager showed off her work as an example of what good looks like and told our VP how excellent she was doing, this fueled her in a way that her title never could. Once she started planning a wedding, though, her incentive became pay, which was tied to her title, and therefore, promotion (not just acknowledgment) became her primary motivator.

As always, feedback is a gift, and I welcome any/all feedback on this episode—good or bad. See you next week 👋.

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