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#6020Totally Bossing It31.0 / 100Get badge
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Totally Bossing It

Hosted by Natalie Lennon

Season 3: A podcast for Accountants who want to "Totally Boss It" in their Accounting Firms. Hosted by Natalie Lennon Founder & Director of Two Sides & Two Sides Academy, A Chartered Accountant and Registered Tax Agent with over 20 years experience working with and in various small, medium and multi-national…

35 episodes · publishes monthly · latest 2025-04-10 · ~19 min/episode

Rank

#6020

Substance

31.0

/ 100

Breakdown

Scored 2026-07
Updated monthly

Ops rank

#450 of 458

Best B2B Ops Podcasts →

Across the index

#6020 of 6181

Substance

Top 97%

outscores 3% of the index

Why it scores where it does

Totally Bossing It ranks #6020 on The B2B Podcast Index with a substance score of 31.0 out of 100, scored across 1 recent episode. It scores highest on guest caliber and specificity & evidence. There is no guest at all - the episode is a solo, unstructured monologue. The host has legitimate credentials (chartered accountant, former partner, firm founder) but demonstrates none of that expertise in this episode; it reads as a personal diary entry rather than practitioner insight.

The five-dimension breakdown

Averaged across 1 recently scored episode, with cited evidence.

Insight Density

6.0 / 20

The episode is almost entirely filler - a personal check-in explaining why the podcast is going quiet during tax season. The only remotely tactical point (send clients a deadline warning email) is obvious to any practitioner, and it is buried under extended rambling about COVID PTSD, gym attendance, and wine on weeknights.

“I just wanted to hop on say hi and you know explain why the podcast will drop off a bit uh from now until july”

“it's a similar thing, right? It's tax season. It's when we're in the thick of it. It's crappy. We don't like it. We hate life.”

Originality

6.0 / 20

There is no original thinking whatsoever. The 'washing machine' metaphor is a mildly colourful label for an entirely clichéd observation (busy season is stressful). Every claim - it passes quickly, we care about clients, self-care matters - is a platitude circulating in every accounting community.

“it's a small period of time in the financial year. And yes, it happens every year. We should be more well-prepared”

“we generally really care about our clients and making sure that they're looked after”

Guest Caliber

7.0 / 20

There is no guest at all - the episode is a solo, unstructured monologue. The host has legitimate credentials (chartered accountant, former partner, firm founder) but demonstrates none of that expertise in this episode; it reads as a personal diary entry rather than practitioner insight.

“I'm Natalie Lennon. I'm the founder and director of Two Sides, an 100% remote accounting and bookkeeping firm”

“I became a partner at 28 and five years later, I sold my 40% share and started Two Sides”

Specificity & Evidence

7.0 / 20

The only concrete details are the May 15 lodgement deadline and the end-of-April client-information cutoff - both well-known statutory facts for Australian tax agents, not original data. No metrics, no firm-specific outcomes, no named tools or processes are shared.

“trying to get every everyone every old bugger who's left their tax returns to the last minute to meet the May 15 deadline”

“we did send out some emails the other day basically saying if we don't have your tax return information by the end of April we may not actually be able to do your tax return for you this year”

Conversational Craft

5.0 / 20

There is no guest, no interviewing, no questions, and no dialogue of any kind. The episode is an unstructured apologetic monologue with no arc, no follow-ups, and no productive tension - purely a note to listeners that content is being paused.

“I guess I just wanted to hop on say hi and you know explain why the podcast will drop off a bit”

“that's enough rambling from me”

Standout episodes

  • S3E13 - Peak Tax Season

    2025-04-10

    31

Rank over time

First period on the Index - history builds from here.

Episodes

1 scored on substance · 35 tracked in total.

  • S3E13 - Peak Tax Season

    2025-04-10 · 6 min

    31 / 100

Frequently asked

What is Totally Bossing It's substance score?
Totally Bossing It scores 31.0 out of 100 for substance and ranks #6020 on The B2B Podcast Index. That puts it ahead of 3% of the B2B podcasts we rank and #450 of 458 in Ops. The score reflects insight density, originality, guest caliber, specificity and conversational craft across recent episodes - not downloads.
Is Totally Bossing It worth listening to?
Totally Bossing It is ranked on The B2B Podcast Index with a substance score of 31.0/100. See the five-dimension breakdown above to judge whether it fits what you're after.
Who hosts Totally Bossing It?
Totally Bossing It is hosted by Natalie Lennon.
How often does Totally Bossing It publish?
Totally Bossing It publishes monthly, has 35 episodes, released its most recent episode on 2025-04-10.
Which Totally Bossing It episode should I start with?
Our highest-scoring recent episode is "S3E13 - Peak Tax Season" (31/100) - a good place to start.

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Topics this show covers

The themes that come up most across this show's episodes.

COVID-19 business impactTwo Sides accounting firmTwo Sides AcademyFBT year-endMay 15 tax return deadlineTax planning deadlinesJob KeeperClient information collection processesFinancial advisor awards

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